[3.5] Rogue optimization

[Legault]

Hello, I need some help on character optimization. I have a lvl 8 halfling rogue with 10 str, 16 dex, 12 con, 16 int, 10 wis and 14 cha after halfling bonuses. Ranks are below. I'm the skill monkey for the party and the official trap checker. The DM has been item-happy lately and now I have Winged Boots, Ring of Invisibility, Studded Leather of Move Silently (+10), Cloak of Elvenkind, Gloves of Dex, a Flaming Punching Dagger and a Luck Blade 0 wishes. Currently, I have as feats Weapon Proficiency: Longbow, Point-Blank Shot and Rapidshot.
As it is the first time many players in the party, including myself, are playing D&D, the DM is giving us a free rearrangement of feats and a little moving around in ranks (not much though) to qualify for a prestige class we want. I planned to take my rogue into lots of sneak attacks by entering Shadowdancer and using HiPS, abusing invisibility, and dip in Swordsage for Assassin's Stance and other maneuvers, but I'm not quite sure if melee is the way to go and if the Shadowdancer is worth all the feats. I'd like to hear the opinion and suggestions of more experienced players. Thanks in advance.

Bluff 7
Diplomacy 10
Disable Device 10
Disguise 5
Forgery 5
Gather information 9
Hide 11
Listen 11
Move Silently 11
Open Lock 9
Search 11
Sense Motive 11
Sleight of Hand 11


Allowed books: PHB I and II, the Dungeon Master Guide, all the completes (except Psionic) and Tome of Battle.

[(Un)Inspired]

Hello, I need some help on character optimization. I have a lvl 8 halfling rogue with 10 str, 16 dex, 12 con, 16 int, 10 wis and 14 cha after halfling bonuses. Ranks are below. I'm the skill monkey for the party and the official trap checker. For starters, allowed books are PHB I and II, the DMG, all the completes and Tome of Battle. The DM has been item-happy lately and now I have Winged Boots, Ring of Invisibility, Studded Leather of Move Silently (+10), Cloak of Elvenkind, Gloves of Dex, a Flaming Punching Dagger and a Luck Blade 0 wishes. Currently, I have as feats Weapon Proficiency: Longbow, Point-Blank Shot and Rapidshot.
As it is the first time many players in the party, including myself, are playing D&D, the DM is giving us a free rearrangement of feats and a little moving around in ranks (not much though) to qualify for a prestige class we want. I planned to take my rogue into lots of sneak attacks by entering Shadowdancer and using HiPS, abusing invisibility, and dip in Swordsage for Assassin's Stance and other maneuvers, but I'm not quite sure if melee is the way to go and if the Shadowdancer is worth all the feats. I'd like to hear the opinion and suggestions of more experienced players. Thanks in advance.

Bluff 7
Diplomacy 10
Disable Device 10
Disguise 5
Forgery 5
Gather information 9
Hide 11
Listen 11
Move Silently 11
Open Lock 9
Search 11
Sense Motive 11
Sleight of Hand 11


What is your goal for this character?

DO you want them to be the absolute best at skill monkeying?

Raining Sneak Attacks into his enemies?

Being a Jack-of-All trades; able to TCOB no matter what sittuation comes up?

What I will suggest depends heavily on what you want to be capable of.

[Legault]

Thanks for the reminder. Skill monkeying is this character's objective, yes, he takes pride in it. However, this playthrough isn't rich on UMD items, which is why I'm not putting points in it. While also being a social figure, he is not the face of the group. Instead he's the go-to-guy when someone needs to be conned, lied to or other not-so-pleasant forms of "diplomacy".
Raining sneak attacks would basically be his Modus Operandi. It is not necessary to be a Jack-of-all-Trades, as the party is fairly varied and we can answer to various situations. Instead, they depend on him for trapfinding and scouting. On the other hand, he doesn't have quite a good combat record. While I'm not looking to make him a combat specialist, I would like for him to be able to help on combat. I consider that sneak attacks are the best way to do so with help of the Ring of Invisibility.

[(Un)Inspired]

Thanks for the reminder. Skill monkeying is this character's objective, yes, he takes pride in it. However, this playthrough isn't rich on UMD items, which is why I'm not putting points in it. While also being a social figure, he is not the face of the group. Instead he's the go-to-guy when someone needs to be conned, lied to or other not-so-pleasant forms of "diplomacy".
Raining sneak attacks would basically be his Modus Operandi. It is not necessary to be a Jack-of-all-Trades, as the party is fairly varied and we can answer to various situations. Instead, they depend on him for trapfinding and scouting. On the other hand, he doesn't have quite a good combat record. While I'm not looking to make him a combat specialist, I would like for him to be able to help on combat. I consider that sneak attacks are the best way to do so with help of the Ring of Invisibility.

I'd recommend at least 3 levels in the base class factotum from dungeonscape in that case. You've got a good int and this class lets you add int to just about anything, including permanently adding it to all str dex and con skilling and ability checks (including initiative).

It gives you a pool of inspiration points that refresh every encounter and let you add you into to you ac, saves, attack and damage. It also lets you add your factotum level to each skill once per day.

They also get all skills as class skills and nearly as many skill points as a rogue.

Eventually you can even burn inspiration points for extra actions.

[Legault]

I thought about that, but Dungeonscape is not part of the allowed books :/

[cerin616]

I'd recommend at least 3 levels in the base class factotum from dungeonscape in that case. You've got a good int and this class lets you add int to just about anything, including permanently adding it to all str dex and con skilling and ability checks (including initiative).

It gives you a pool of inspiration points that refresh every encounter and let you add you into to you ac, saves, attack and damage. It also lets you add your factotum level to each skill once per day.

They also get all skills as class skills and nearly as many skill points as a rogue.

Eventually you can even burn inspiration points for extra actions.

Seconding this. With Brains over Brawn, a tripping weapon and a couple feats, you can become a terror of battle utility.

With factotum and jack of all trades, all skills are class skills, and all skills are considered trained, the biggest advantage of this being an effective "knowledge(everything)".
Combine this with collector of stories (+5 to knowledge when used to identify weaknesses/etc. in creatures) and knowledge devotion (make knowledge check to gain insight bonus to attack and damage) to can make a check against any creature to gain an insight bonus, and have a +5 to that check.

EDIT: oh no! you cant dungeonscape! Ill brain some other things then

[(Un)Inspired]

I thought about that, but Dungeonscape is not part of the allowed books :/

Derp! how did I miss that?

Well, it might not be what you're looking for, but have you thought about multiclassing wizard and then complete mage's unseen seer?

You'll have almost as many skill point and you'll be able to giving devastating telekinesis delivered sneak attacks. You'll also be able to back up all you're skill awesomeness with spells like invisibility.

[Legault]

I considered multiclassing Assassin and then Unseen seer, but I'm not quite sure how schools of magic work.

[(Un)Inspired]

I considered multiclassing Assassin and then Unseen seer, but I'm not quite sure how schools of magic work.

Could you expand upon this? If there's anything I could do to help explain spellcasting to you I'd be happy to try.

[Legault]

The Unseen Seer prestige class says that each level increases an arcane spellcasting class. I also know that there is a divine spellcasting class. But I wouldn't know where the Assassin's spellcasting class would fit.

[torrasque666]

The Unseen Seer prestige class says that each level increases an arcane spellcasting class. I also know that there is a divine spellcasting class. But I wouldn't know where the Assassin's spellcasting class would fit.
Assassins cast Arcane spells. Its listed under the Spellcasting​ class feature.

[Legault]

So if I dip into Assassin and then 3 levels into Unseen Seer, then I would be able to cast greater invisibility? (Lvl 4 spell for Assassin)

[torrasque666]

So if I dip into Assassin and then 3 levels into Unseen Seer, then I would be able to cast greater invisibility? (Lvl 4 spell for Assassin)
Assassins don't get a 4th level spell until 7th level. So you'd need a 4 level dip into Assassin to get it with 3 levels of US. Which is kind of more of a scoop than a dip.

[(Un)Inspired]

So if I dip into Assassin and then 3 levels into Unseen Seer, then I would be able to cast greater invisibility? (Lvl 4 spell for Assassin)

No quite. Assassins don't gain access to 4th level spells until they have 7 levels of classes that advance assassin spellcasting.

Spell's levels are correlate to a caster's level but they are, in fact, different.

[Legault]

What about some less magic-intensive alternatives?

[OldTrees1]

Skillmonkey guides:
http://www.giantitp.com/forums/showthread.php?88715-Chronos-s-Unalliterative-Skillmonkey-Guide-3-x
http://brilliantgameologists.com/boards/index.php?topic=11034
http://community.wizards.com/forum/previous-editions-character-optimization/threads/968271
http://brilliantgameologists.com/boards/index.php?topic=6180
http://brilliantgameologists.com/boards/index.php?topic=4858
http://brilliantgameologists.com/boards/index.php?topic=10996


I would definitely suggest picking up Hide in Plain Sight.
Skill Mastery from 1 level of Exemplar at 11th level would be a good idea too.

[Legault]

Thanks, I will be checking them

[(Un)Inspired]

I'd like to second the recommendation to read Chronos Skill monkey guide. It's full of pretty good info and I found his approach enjoyable.

Honestly though, if you want a direct increase is combat abilities without much of a skill point drop then I recomend that you just dive into Swordsage levels. It's jsut so so so much more dnagerous in combat that a straight rogue. It only has two less skill points per level.

I know that the argument that it still has a lot of skill points brushes dangerously close to sorites paradox but your int is so high that I think you could still have a satisfying number of skills maxed out.

[Legault]

I was considering the Swordsage path.

I was trying to figure out a (legal) way to abuse my ring of invisibility. Some way in which I can sneak attack, move away and hide/use invisibility. Rinse and repeat. However, I don't think that's possible.