how to build and use a rogue

[King of Nowhere]

I am going to need a rogue of level 15 to 17, high wealth, to join my gallery of boss enemies. But I don't really know what to do with one.

I mean, flank someone and sneak attack, ok. But even then - and even with me houseruling that if you have twin weapons you can attack with both as a standard action - the damage output is still not matching that of a straight up melee build. There is also the low BAB, meaning that you have troubles actually hitting a well armored opponent. But most damning, rogues are terribly squishy. For all their dex, I can't have them match the AC of some guy with heavy armor and animated shield. Coupled with low hit points, it means that the rogue will attack once, then die. Low fort and will saving throws Also means being very exposed to any save-or-die thrown at you (on the plus side, you're mostly immune to most area damage).

Well, I'm sure there's much more that can be done with a rogue than being this squishy guy who only deals damage when flanking, and not as much as anyone else anyway. Ok, a rogue has a lot of out-of-combat utility, but that's besides the point here, because this npc is supposed to fight.

I still haven't decided if it should be an archer or stabber rogue, so both propositions are open.

I try to optimize, but I ddon't go crazy on it, so suggestions including a half dozen dips or three prestige classes are too hardcore for my table. I prefer core because my knowledge of splatbooks is sketchy at best, but I have nothing against adding a bit of extra material. As I run a high magic, high wealth world, getting magic items for specific effects is not difficult, but at the same time most strategies that can be countered with simple items will be countered. For example, there's little point in trying with greater invisibility, because pretty much everyone important can see invisibility.

Thanks in advance for your contributions.

[Mike Miller]

The Craven feat will boost damage. Finding ways to get sneak attack is next. The first level stance, Island of Blades, is an easy way to flank with an ally and thus gain sneak attack. Anything that increases SA or removed an opponent's Dex is good.

[tstewt1921]

I have found that rogues work better in pairs. If they high wealth there are items that give them free jaunts or mini teleports that when the barbarian comes charging right before he finishes his attack you jaunt off to the side to avoid said attack. You get several little things and equip them specifically against whatever you are sending them at, as most rogues would think smart about what they are going to fight. Think like assassins without the 1 hit kill. They would pounce the wizard and then use tactical cunningness to out do the rest of the party.

Also, just because "important people" can see invisible stuff it doesn't mean the party you are sending them after can.

[tstewt1921]

When you say high wealth, can you give an amount you want to spend and I can try and put something together for you?

[King of Nowhere]

Also, just because "important people" can see invisible stuff it doesn't mean the party you are sending them after can.

this is going to be an npc villain, and I'm going to send him against the pcs, whom I know are well equipped for invisibility. On the plus side, I am pplanning to place him somewhere with a lot of cover, so mundane hiding still works. and he'll have a flanking partner

[AnimeTheCat]

A single level dip of conjuration specialist wizard with rapid summoning and abrupt jaunt would serve any cunning character well. Standard action (or with quicken spell metamagic rods, swift action) summons for flanking, disruption, and utility would be irreplaceable. Abrupt jaunt for defensive measures of course.

It's 99% rogue, with wizard for utility.

[RaiKirah]

If you're concerned about damage output I would second the suggestion to get Craven. Pair that with sources of extra attacks and you can dish out the damage. Assuming Human and level 15 you have 7 feats to play with, so something like

Two Weapon Fighting
Improved Two Weapon Fighting
Darkstalker
Craven
Dodge
Mobility
Elusive Target

gets you 4 attacks on a full attack with +7d6+15 SA damage each. Picking up a level of Shadowdancer (or just a Collar of Umbral Metamorphosis) gets you Hide in Plain Sight, and Elusive Target makes you immune to Power Attack Damage from one enemy each round. If Flaws are on the table pick up Travel Devotion for swift action teleport and maybe Staggering Strike to add some cc to your single target damage. You're still squishy, but you have some options and do a lot of damage. If you can get some extra feats from dipping, picking up Sun School and Snap Kick makes it 6 attacks on a full attack after teleporting. A couple levels of Swordsage around ECL9 add some nice options as well.

[Biffoniacus_Furiou]

A bit over the target CR, but take some pointers from this opponent:
http://www.giantitp.com/forums/showthread.php?358732-I-need-a-lot-of-easily-playable-builds#4
(One of the links in that post is no longer good, here's a current one for Psychic Assassin (http://archive.wizards.com/default.asp?x=dnd/psm/20040723d).)

[Falontani]

if you haven't chosen a race then a pair of twins (Dvati come to mind) would allow you to target two players at once, or set up sneak attacks very well. Pure rogues are great, but they really suffer in the department of doing more than Sneak up and sneak attack someone. If your doing high gold then give the rogue some potent poisons to use, and true seeing/see invis is great until the rogue drops some concealment via Solid Fog. And while the group is working on getting freedom of movement on everyone the rogue could with spring attack and FoM precast drop a wizard.

Paralysis poison works great on rogues and bards, high int damage poison would be great for a wizard. I dont have the build on hand but I'm sure someone could link you a great rogue build that deals a ton of cha damage.

Also remember to use complete scoundrel/adventure's ambush feats

[Nebuul]

If I may - your PCs can use true seeing and see invisibility all day long, but if your villainous rogue has a high hide skill, it won't help them. Use that to your advantage.

And give him a way to have silence around himself.

[tstewt1921]

Stealthy Mcstealtherson:

Human

Rogue 7, Nightsong Enforcer 8.

Feats: 1. Improved Initiative (Requirement for NE), Weap Finesse
3. Craven
6. Martial Study (Assassins Stance) (Unless you want to dip to something in ToB)
9. Martial Stance (Shadow Blade)
12. Dark Stalker
15. Sickening Strike

Items:

Armor: Armor of Slick and Shadow (Pick the level)
Weapon: Keen, Lucky, Vanishing (also look at
weapon crystals in the MiC)
Arms: Bracers of Lightning
Body: Shadow Veil
Feet: Dimension Stride Boots
Shoulders: Shadow Cloak
Hands: Gloves of Fortunate Striking
Head: Helm of Teleport (Being able to escape helps)
Ring: Ring of Lightning Flashes
Ring: Ring of X-Ray Vision (Again to Escape)
Throat: Scentblinder (Ran out of ideas but seemed nifty)
Torso: Vest of Free Movement (No Stopping Your moves)
Waist: Belt of Battle

This is just a brief overview, and a very defensive character, if you give him a proper ranged partner they could be deadly together. It's all about magic item selection, you may not be able to pump out a lot of damage early, but dammit they wouldn't be able to hurt you for a while.

[BowStreetRunner]

Batman vs Superman, who won? Batman, of course! Why? Because Batman CHEATS!!! Yes, he used Kryptonite. That's how a rogue wins fights.

When running a Rogue encounter you have to remember that rogues cheat and take every advantage they can. They reconnoiter their opponents in advance to determine their weaknesses. They use hit and run tactics, sneaking into position to launch an attack and then disappearing again before the enemy can respond. They use distractions and deception. They use traps. And they don't stick around unless they are sure they can win.

An effectively-run rogue encounter will often involve a probing attack with the rogue slipping away. The party then has to try to pursue the rogue, tracking them down as best they can. The rogue hits them again along the way and then slips away just as adroitly as before. The party gets frustrated because a rogue won't stand and fight fair.

Rogues use allies - sometimes willing ones like an associate or some lackeys. But they also use unwilling allies, like luring the party past some large, powerful monster's lair which the rogue can sneak past but the party cannot. Or they will deceive others into fighting their battles for them, convincing the town guard that the party are a bunch of bandits and then not sticking around while the guards and the party battle it out.

If you run a rogue encounter as a standard combat encounter, the rogue won't last very long. They were never meant to. Look over the entire list of the rogue's skills and abilities and ask yourself, 'how can I use this?' That's when the rogue is at its best.

[Eldariel]

I conveniently have a level 15 Rogue (well, Rogue 13/Swordsage 2 for some mobility and full attack options) lying around here (https://www.myth-weavers.com/sheetview.php?sheetid=128332). It was made for Test of Might originally but never got played. Basically the idea is to run Wilderness Rogue (http://www.d20srd.org/srd/variant/classes/variantCharacterClasses.htm#wildernessRogue) to get Ranger Camouflage and Hide in Plain Sight by level 13 and use Hide/Move Silently as the first line of defense. Add on that UMD and various magical gadgets (he has a reasonable collection of Wands, though you should switch around his scrolls adding stuff like Gate if you want him to go down that path) combined with Ring of Blinking and Eversmoking Bottle and he has a reasonable collection of ways to sneak attack and reasonable options (I used Wand of Orb of Force CL10) to attack SA-immune enemies. If I had all sources available, I'd 100% give him Craven [Champions of Ruin] and Penetrating Strike [Dungeonscape] to increase sneak attack damage and enable it against all opponents (halved but that's much better than nothing at all).

The equipment is way too expensive since it's all crafted so you should cull about half of it and obviously all the buffs (the party had a Wizard and a Cleric), but it's mostly numbers (and Wands could be used to e.g. regain Greater Magic Weapon and Magic Vestment); the important parts are the Wands/Scrolls and the sneaking enablers. Also he's stocked full of rerolls (Luckblades and Mantle of Second Chances) since nothing feels more appropriate for a Rogue. Could add Alter Fortune [PHBII] Wand to a wandchamber (but again, Wand Chambers are Dungeonscape, which wasn't an allowed source). Also, ToM was no Polymorph; if you do use Polymorph, Rogue turning into e.g. a 12-headed Hydra can do ugly damage (while also gaining the ability to move and attack).


And yeah, sneak around, steal all PCs' stuff (Sleight of Hand is great), do things like that instead of fighting directly. Then when they can't defend themselves properly, end their miserable lives (preferably while they're stuck fighting something else; Bluff/Diplomacy [doesn't affect PCs is bull****] them to undertake some dangerous quest and then backstab them; masquerade as a friend and betray them at the worst possible time).

[Matrota]

Definitely pick up hide in plain sight and darkstalker, boosting hide and move silently as much as possible. Hiding is a move-equivalent action, So travel devotion is your friend. Have them travel devotion to move up to an enemy while hidden, attack, and then move directly backwards while hiding to vanish until their next turn. It's similar to a blink spell, only better. Freedom of movement will seriously help this out if you can pick it up somehow. This way when they briefly show up, the party can't CC them. I almost wiped a party before using this sort of strategy at a much lower level, and he was only stopped because he got grappled and was going dingdingding on the party dread necromancer's detect magic radar. On that topic, a rod of nystul's undetectable aura is pretty cheap, and so outiftting your rogue with that would make him undetectable to magic senses as well.

[King of Nowhere]

For some reasons, I assumed that rogues lost some class ability when using shields. Now that I see animated shields are fully viable, they can actually get a better AC than normal fighter types.


When you say high wealth, can you give an amount you want to spend and I can try and put something together for you?

generally half a million to a million gp, though it's less than a target and more a "give whatever I feel is appropriate without worrying much about price"


I conveniently have a level 15 Rogue (well, Rogue 13/Swordsage 2 for some mobility and full attack options) lying around here (https://www.myth-weavers.com/sheetview.php?sheetid=128332).

interesting, though most of it is stuff I'm not familiar with (and the party also isn't). your magic items are, however, incredibly conveniently crafted. and you are relying on having 9 spells every day. well, i can fix most of it with items and increased wealth.
main problem is the attack bonus. +25 for the first attack is definitely low for that level. most of the party has an AC between 35 and 40, +25 to hit is too unreliable. although it becomes workable since she'll be flanking and her partner will provide a lot of trips for another +4 to hit. still, anything that can increase the hit bonus is welcome.



And yeah, sneak around, steal all PCs' stuff (Sleight of Hand is great), do things like that instead of fighting directly. Then when they can't defend themselves properly, end their miserable lives (preferably while they're stuck fighting something else; Bluff/Diplomacy [doesn't affect PCs is bull****] them to undertake some dangerous quest and then backstab them; masquerade as a friend and betray them at the worst possible time).
I tried all those things in the past, at much lower levels, but without much luck. Well, actually "angel-face Nino" was a cool opponent; dragging the party into a fight while pretending to be their allies, only to backstab them after they engaged. bluffing with the guards who arrived soon after so that they actually arrested the party. using disguises to shoot poisoned darts and disappear into the crowd. In the end, though, a barbarian fast movement and a flying animal companion to give directions allowed the party to chase him to the end. pity, he had enough backstory to make a nice recurring villain.
he fell victim of his weaknesses; the party cringed when their supposed ally suddenly sneak-attacked them, but the next round the fighter turned aroound to face this new threat and put him down in no time. after he bluffed the guards once, they would be on the ready and not fall anymore for the same trick. and when his escape strategy was removed, he was captured. Still rotting in prison somewhere.
the first rogue I sent against them instead completely crapped all her rolls and ended up grappled before she could do anything of notice. she was put on a work-release program and is now acting as a spy on behalf of the party.

[Eldariel]

interesting, though most of it is stuff I'm not familiar with (and the party also isn't). your magic items are, however, incredibly conveniently crafted. and you are relying on having 9 spells every day. well, i can fix most of it with items and increased wealth.
main problem is the attack bonus. +25 for the first attack is definitely low for that level. most of the party has an AC between 35 and 40, +25 to hit is too unreliable. although it becomes workable since she'll be flanking and her partner will provide a lot of trips for another +4 to hit. still, anything that can increase the hit bonus is welcome.

Well, big one is denying the enemy bonuses. If the enemy can't beat your Hide or you're Blinking or have otherwise secured the status of an invisible attacker, that's +2 and a lot of penalties to the enemy AC (and of course, they can't attack back without guessing your square while you keep 5' stepping around so it's almost complete protection as well). Boots of Speed of course grant +1 from Haste, and you can always use Reduce Person for +2 Dex and +1 Size (at the cost of becoming Tiny and having no reach). These are easily doable. A more expensive option would be Heroism.

Of course, the nuclear option would be something like Wraithstrike [Spell Compendium] in Wand Chambers [Dungeonscape] for the swift action "make all my attacks as touch attacks"-option. If you combine this with hiding in plain sight, you're looking at attacking flat-footed touch AC (usually 10) vs. all but the most observant characters. You could also use those scrolls of Antimagic Field or Disjunction to simply remove the magical components of their AC and go to town.

Devotion-feats from Complete Champion such as Chaos Devotion/Law Devotion, Animal Devotion and Knowledge Devotion are the biggest one-feat numeric buffs in the game so if you just want to give him numbers, have him pick one of those up and use it in the fight. The build has some loose feats; Quick Draw is mostly for Wands (where it doesn't even work by RAW but did in this run) and Tactile Trapsmith is kinda whatever; just there to ensure sufficient numbers for trapfinding and disarming. But even without it, he'd be looking at +30 or something which tends to be more than enough. And he isn't doing an arena run but is an actual character in an actual game so he can just skip disarming the traps too difficult for safe disarming.

Note though, he's perfectly content just sniping with Orbs of Force from total cover faraway. If necessary, these can be combined with True Strike. It's only 19d6 damage per round (average 66,5) so it's in no ways life threatening to the party but it'll eventually add up. Indeed, heading into melee should be plan C. Magic, range, unfair advantages, and stealing party items/slipping the party cursed items is much more Roguey and harder to fight. You should definitely give him Permanency + Arcane Sight used from scrolls as that's a surefire way to locate most important targets within 120' and works in various fogs and the like (in the party, Wizard + Telepathy rendered this unnecessary). You could also give him a +1 Seeking Bow too and a Wand of Sniper's Shot; a good plan B particularly with Fog and the like. As Seeking negates concealment and Sniper's Shot negates range limits, it doesn't matter from where he attacks from as long as he can pinpoint the target (Arcane Sight is a great tool to that end for anything within 120' even through Fogs or the like; he doesn't even need Spellcraft to figure out which enchantments he's seeing, just that he's seeing targets with plenty of magic auras).

Again, give battle when you have the advantage. Perhaps scrolls of Solid Fog, Wall of Force, etc. could be used to enable him to engage party members 2v1 rather than 1v4. It's just not at all realistic to win a fight as a squishy melee type when outnumbered.


I tried all those things in the past, at much lower levels, but without much luck. Well, actually "angel-face Nino" was a cool opponent; dragging the party into a fight while pretending to be their allies, only to backstab them after they engaged. bluffing with the guards who arrived soon after so that they actually arrested the party. using disguises to shoot poisoned darts and disappear into the crowd. In the end, though, a barbarian fast movement and a flying animal companion to give directions allowed the party to chase him to the end. pity, he had enough backstory to make a nice recurring villain.
he fell victim of his weaknesses; the party cringed when their supposed ally suddenly sneak-attacked them, but the next round the fighter turned aroound to face this new threat and put him down in no time. after he bluffed the guards once, they would be on the ready and not fall anymore for the same trick. and when his escape strategy was removed, he was captured. Still rotting in prison somewhere.
the first rogue I sent against them instead completely crapped all her rolls and ended up grappled before she could do anything of notice. she was put on a work-release program and is now acting as a spy on behalf of the party.

Well, clearly the first backstabber wasn't doing the prep work. Sleight of Hand allows slipping cursed items and stealing weapons from the targets you're about to doublecross and of course it needs to happen while the party is already in a life-or-death struggle (or just kill some in their sleep); otherwise you just at best kill one of them and then get summarily slaughtered by the others. A rogue should try to engineer as unfair a situation as possible. No intelligent Rogue goes 1v4; Rogues are about having the unfair advantage, not the unfair disadvantage. If he can't get help (he should use his skills to plot the party into some trouble with something really big), he should divide and conquer and again, try to team up with something to take the party members down one by one. Lies, deceit, and particularly magic can be great tools to engineer the scenario necessary but the Rogue needs to use their wits first and foremost to ensure the situation is such that the party can't see him and that he can attack without retaliation. No matter how good his tricks and numbers, he isn't beating full casters of these levels easily.

Rogues are all about being unfair. They aren't as powerful as casters nor as durable as warrior-types and their damage doesn't compare to other classes even when they get their Sneak Attack off. They definitely aren't hardy enough to take on multiple opponents at once. Thus they need to use their strengths; skills, Use Magic Device in particular, acquisitions/items, contacts, etc. to engineer a situation where their opponents can't bring their strengths to bear or where they have a sufficient advantage over their enemies for it to not matter. The listed character has Camouflage and Hide in Plain Sight with +41 Hide/Move Silently for example. This means that any character with under +21 Spot is unlikely to ever see him even if he's right next to him. If buffing the Hide/Move Silently higher (switch to Whisper Gnome, add Greater Stealth/Silent Moves over Improved enhancements, use Reduce Person, etc.) it's further possible to just full attack in peoples' faces and eat up the -20 while still making the Hide checks thus killing people while camouflaged. That's the kind of advantage that enables a Rogue to win and the kind they should look for. Same with Sniper's Shot + attacking from 100' or more away from a hiding position and just mercilessly raining death upon the party with them having no idea where the attacks are coming from.

And replacing someone's Ring of Protection with a Ring of Clumsiness (http://www.d20srd.org/srd/magicItems/cursedItems.htm#ringofClumsiness), their Longsword with a -2 Sword (http://www.d20srd.org/srd/magicItems/cursedItems.htm#swordCursed), or even better, Berserking Sword to have them slay their teammates (while the Rogue is safely hidden away), etc.

[King of Nowhere]

Well, clearly the first backstabber wasn't doing the prep work. Sleight of Hand allows slipping cursed items and stealing weapons from the targets you're about to doublecross and of course it needs to happen while the party is already in a life-or-death struggle (or just kill some in their sleep); otherwise you just at best kill one of them and then get summarily slaughtered by the others. A rogue should try to engineer as unfair a situation as possible. No intelligent Rogue goes 1v4; Rogues are about having the unfair advantage, not the unfair disadvantage. If he can't get help (he should use his skills to plot the party into some trouble with something really big), he should divide and conquer and again, try to team up with something to take the party members down one by one. Lies, deceit, and particularly magic can be great tools to engineer the scenario necessary but the Rogue needs to use their wits first and foremost to ensure the situation is such that the party can't see him and that he can attack without retaliation. No matter how good his tricks and numbers, he isn't beating full casters of these levels easily.


I tried the pickpocketing thing with the other rogue, she failed the check and got captured like that. The party rogue has a decent spot check, so robbing the party like that is potentially dangerous, with a very high risk for a relatively low reward. And regardless of whether the rules actually say it, stealing an item that is in direct contact with the skin, especially one fitting tightly like a ring, is going to carry a considerable penalty. Slipping a cursed item in a pocket is something I didn't consider; I don't know any that can work without being worn, but I'll go look for some.

As for engineering an unfair situation, the party was fighting a big scary fighter when 'angel-face' betrayed them, so a double sneak attack with poisoned daggers could have been dangerous. turned out, the fighter wasn't big and scary enough, and one of the sneak attacks missed anyway. but then, the party is actually supposed to win.

I think I'll go with ranged rogue. I am planning the party to face a big scary fighter (again) in the middle of a slum, a rogue hiding and shooting arrows at the casters should have a much smaller chance of failure. possibly the party rogue will be too distracted during the fight, and everyone else won't be able to beat her hide check even with the -20 for sniping.

[Eldariel]

I tried the pickpocketing thing with the other rogue, she failed the check and got captured like that. The party rogue has a decent spot check, so robbing the party like that is potentially dangerous, with a very high risk for a relatively low reward. And regardless of whether the rules actually say it, stealing an item that is in direct contact with the skin, especially one fitting tightly like a ring, is going to carry a considerable penalty. Slipping a cursed item in a pocket is something I didn't consider; I don't know any that can work without being worn, but I'll go look for some.

As for engineering an unfair situation, the party was fighting a big scary fighter when 'angel-face' betrayed them, so a double sneak attack with poisoned daggers could have been dangerous. turned out, the fighter wasn't big and scary enough, and one of the sneak attacks missed anyway. but then, the party is actually supposed to win.

I think I'll go with ranged rogue. I am planning the party to face a big scary fighter (again) in the middle of a slum, a rogue hiding and shooting arrows at the casters should have a much smaller chance of failure. possibly the party rogue will be too distracted during the fight, and everyone else won't be able to beat her hide check even with the -20 for sniping.

That's still just 2v4. He'd want to make it like 8v4 or something; a proper brawl where he can slip in and do damage. The party cluing in on his plans would allow them to even the odds or so, so it wouldn't even be unfair in that sense. Don't forget range penalties to Spot; it's very easy to Hide 100' away (-10 to Spot-checks). Not all fights need to be fair; the onus of taking fair fights lies with the PCs.

[Doctor Awkward]

I'm a big fan of poison use builds.

A Rogue 5/Assassin 10 with Master of Poisons, Poison Expert (injury poisons), Poison Master (injury)*, the Venemous Strike and Sickening Strike ambush feats, can get some pretty scary-high save DC's with even silly low-level stuff like Sasson-Leaf residue, let alone the scary stuff like purple worm venom or black lotus extract.

Also useful is an Assassination weapon enchancement, which adds the weapon's enhancement bonus to save DC for poisons (combine with Oil of Greater Magic Weapon for more saving-boosting goodness).

To handle the invisibility issue, consider taking Advantage of the Hide in Plain sight granted by Assassin 7, which allows him to hide so long as he has concealment. He can cast the Deeper Darkness assassin spell on himself, and then follow up with the 1st level Assassin spell Ebon Eyes which enables him to see clearly in his own magical darkness.
If the party is also equipped to see in magical darkness (and thus negate his concealment from it), giving him the Dark template will grant him a different version of HiPS that functions so long as he is not in direct sunlight. Combine with the Darkstalker feat to negate the party's ability to find him with special senses.

The other thing this will allow you to do, when he is done with the party's ****... is to utilized Death Attack in conjunction with Deeper Darkness to keep himself within line of sight to the party but totally hidden. Then utilizing a mostly spent wand of Deathsight, he can death attack them in only one round instead of three.

In my signature is a build I submitted for the Horsemen of the Apocalypse contest that is a Death Attack specialist if you are interested.

[Hellpyre]

If you have a few levels of Swordsage in there, or throw on some shadow hands, You can get access to Stalker in the Night, which will allow you to move and attack without losing your Hide and Move Silently checks.

[Jay R]

An ideal rogue has allies - people to hold the foes' attention while the rogue stays hidden.

The rogue is a lousy BBEG, but a great minion. In the perfect ambush, the enemies never know the rogue is there. They are busy with the melee fighters and the casters, and don't realize that the extra damage is coming from the shadows.

[TalonOfAnathrax]

Rogue works very well with Hide in Plain Sight, maxed out Hide, and something like Swift Attack or Flyby Attack.
The idea here isn't to make a lot of attacks in one round, but to sneak attack once every single round while remaining hidden and hard to target. Carry an item or two with Darkness cast on it to always have Concealement ot use Hide in Plain Sight, an wear a ring of counterspells with Dispel Magic stored in it.
This kind of rogue wouldn't fight alone of course - he'd have meatshields, magic items and maybe a caster as support, but he'd be the main threat.
Rogues benefit greatly from Skill Tricks and items like the Mantle of the Predator which is cheap and grants extra sneak attack.

I see high-level rogue villains as using their gear to defend themselves from Magic (get Mind Blanc and such) and then harassing players by using massive Stealth, poison and kiting strategies.

You could also make them master manipulators, but then they may as well just be rich Aristocrats.