Help multiclassing a Bugbear Rogue

[JenkhisKhan]

This is my first post on the site. In fact, the only reason I even signed up was so I could search the forum. Since I couldn't find an answer, here we are.

Before I begin, my DM encourages us to make the characters we want to play and not the characters our party needs because "unbalanced parties are more fun." This means I'll be needing help gaining adequate versatility with character theme being the main concern.

That being said:

Starting level 1 with a -5 point buy, 2 weapons, lvl 5 or lower cloth armor, and lvl 5 hand or feet slot.

Dwarf Battlemind
Human Wizard (Arcanst)
Drow Wizard (Mage)
Possibly a Human Avenger
Bugbear Rogue

As of now, my starting build is:

Brutal Scoundrel tactics

14 Str (+2 racial)
10 Con
16 Dex (+2 racial)
10 Int
12 Wis
16 Cha

Acrobatics, bluff, intimidate, perception, stealth, and thievery training.

At will: acrobatic strike, disheartening strike
Encounter: acrobat's blade trick
Daily: Handspring Assault

Versatile Duelist feat

Items:
Weapons: large broadsword, large shuriken
Armor: +1 breaching cloth armor
Hands slot: hedge wizard's gloves

My goal for lvl 11 at this point:

Paragon Path: Jack-of-All-Trades

18 Str
11 Con
21 Dex
11 Int
13 Wis
18 Cha

At will: See above
Encounter: See above, flailing shove, hectoring strike
Daily: See above, hobble, deadly positioning
Utility: fleeting ghost, chameleon, shadow stride

Feats: see above, wild talent master (telekinetic grasp, sensing eye, body equilibrium), master at arms, versatile expertise (heavy blades and light blades), swift footwork, backstabber, and evasive footwork.

Now for the fun stuff!

I thought the idea of a hulking brute tiptoeing behind a guard as he slowly drew an immense sword before cleaving the poor man in half would be pretty hilarious. I was super stoked when I found the bugbear. Also, in addition to having the party from hell - I can assure you that I will have to rely on myself for combat advantage - my DM saw fit to give us each two personality quirks. We picked two numbers between 1 and 20, and I wound up being a kleptomaniac with a gambling addiction. Great... (If you want a full character description and background, let me know.)

I'm looking for a very secretive, very stealthy cutthroat with an obvious obsession with various magic abilities that make him a more effective thief and cheat. The Hedge Wizard's Gloves would be a perfect example. With his high charisma and acrobatics training, he WILL be going a lot of flips, cartwheels, and handsprings for full comedic effect. I'm also going to need access to a few decent control options. My question is how to most effectively multiclass my way into those sorts of abilities. I haven't been too impressed with any of the multiclass options, but I haven't really been able to give the power's I'd be able to take much research.

[MwaO]

First off, a couple of links:
http://www.enworld.org/forum/showthread.php?472893-4E-Character-Optimization-WOTC-rescue-Handbook-Guide

http://www.enworld.org/forum/showthread.php?469717-Han-Shot-First-A-Scoundrel-s-Guide

Okay, let's take a broadsword to the build...
You're not using a legal array. If you do have extra points or rolls for whatever reason and you're a brutal scoundrel, put more points in Str than Cha. And pay up for a 20 Dex after racial bonus +2 for a Rogue. It pays for itself.

Bugbear, Versatile Duelist, Cloth armor, having multiple expertise feats are all not great ideas. The way you do extra damage and big amounts of it are elemental damage+lots of attacks. Not increasing weapon size by +0-2 damage. So I'd wield a dagger. You get +1 to hit with it, it works with Light Blade Expertise, which in itself adds a +1 to damage.

Here's the way to look at it - wielding a Broadsword is +2 to hit and does +0-6 extra damage per W over a Dagger. Wielding a Dagger is +4 for you and gets you +1 damage with CA in Heroic. So in essence, you're trading a +2 to hit, +1 damage for +3 damage(on average) at the cost of a feat. Does that at all sound like a good deal for you?

Cunning Stalker gives you CA against anyone you're next to who doesn't have any other enemies next to them. This is absolutely gold for you. As in completely mandatory and your level 1 feat without question.

Encounter powers to look at are Low Slash, Circling Predator, Snap Shot.

Your party is missing a leader, so I'd look at Warlord to help out. Resourceful Leader is a great entry feat - gives your allies bonuses to damage when they spend an AP. Rousing Words is a strong power swap. Vengeance is Mine & Death from Two Sides are very good powers. And Freedom Fighter is a powerhouse paragon path that makes everyone better - especially when you attack the person attacking the Defender with the e11 and then trigger the Battlemind's Mindspike.

Anyway, I'd check out the Rogue's Handbook. You should really think about what you want as your options.

[JenkhisKhan]

[QUOTE=MwaO;21789176Okay, let's take a broadsword to the build...
You're not using a legal array. If you do have extra points or rolls for whatever reason and you're a brutal scoundrel, put more points in Str than Cha. And pay up for a 20 Dex after racial bonus +2 for a Rogue. It pays for itself.

Bugbear, Versatile Duelist, Cloth armor, having multiple expertise feats are all not great ideas. The way you do extra damage and big amounts of it are elemental damage+lots of attacks. Not increasing weapon size by +0-2 damage. So I'd wield a dagger. You get +1 to hit with it, it works with Light Blade Expertise, which in itself adds a +1 to damage.

Here's the way to look at it - wielding a Broadsword is +2 to hit and does +0-6 extra damage per W over a Dagger. Wielding a Dagger is +4 for you and gets you +1 damage with CA in Heroic. So in essence, you're trading a +2 to hit, +1 damage for +3 damage(on average) at the cost of a feat. Does that at all sound like a good deal for you?

Cunning Stalker gives you CA against anyone you're next to who doesn't have any other enemies next to them. This is absolutely gold for you. As in completely mandatory and your level 1 feat without question.

Encounter powers to look at are Low Slash, Circling Predator, Snap Shot.

Your party is missing a leader, so I'd look at Warlord to help out. Resourceful Leader is a great entry feat - gives your allies bonuses to damage when they spend an AP. Rousing Words is a strong power swap. Vengeance is Mine & Death from Two Sides are very good powers. And Freedom Fighter is a powerhouse paragon path that makes everyone better - especially when you attack the person attacking the Defender with the e11 and then trigger the Battlemind's Mindspike.

Anyway, I'd check out the Rogue's Handbook. You should really think about what you want as your options.[/QUOTE]

I will most certainly check those guides and handbooks out and get back with you. Until then:

I know it isn't a legal array. We're VERY homebrew. In this campaign, we're throwing out the +2 for combat advantage and using the 5e-style roll two and take the higher (or lower). We were given 25 points to point-buy our stats. I can make them whatever I need them to be. The reason I made charisma equal to strength is that 1) I'm addicting to gambling, 2) my character is going to be required to hide his race nearly constantly with disguises, and 3) I'm the only one trained in intimidate. I'm open to either reducing it if you think I'm being overly cautious or taking a different tactic option.

I would take the dagger route if not for my requirement of wielding a massive sword. I'm willing to sacrifice a bit of ruthless optimization in the name of fun, so, in that context, the dagger/broadsword tradeoff is a deal I'm willing to make. I'm not saying I wouldn't be open to changing, I just think I really want a ridiculous sword no matter how illogical it is.

I will most certainly look at Cunning Stalker at lvl 2 or 3 if I keep the sword. The decision will probably hinge on how well my party flanks and I can sneak my way into CA.

Definitely like those powers more than the one's I had chosen. It took me a second to see why Snap Shot was even mentioned... lol

Warlord was my first thought, but we hardly ever get action points. I don't know if this is because our DM is sadistic, we are invariably a party of belligerents and try to kill everything that says "no," or what. All of those skills look amazing. I'll probably look for something to replace Death from Two Sides if our party doesn't include another striker.

Thanks for all the help! It's a lot to think about. I'll mull it over and get back to you.