Min/Max Boards

You could 2WF with the proper dips - actually just one level of such. A Hit-And-Run (DotU) Fighter grants you a +2 to Initiative and +Dex-to-damage against flatfooted foes. Your bonus feat becomes Aereni Focus (Iaijutsu Focus) and the Fighter Bonus feat is EWP:Gnomish Quickrazor.

Yes, this shoehorns you into fighting with something that effectively is an Assassin's Hidden Blade (and how is that a flaw, actually...), but you can easily obtain a +9d6 to damage against your flatfooted opponents. With spellcasting AND Diamond Mind manevers you shouldn't have problems with actually getting your enemies in that condition. Sneak Attack is - also- a dip+feat away. Simply make that Hit-And-Run fighter a Sneak Attack (UA) variant. Now, that +1d6 sneak attack isn't particularily impressive, but it opens the Craven feat, giving you a +CL SA damage. 2-level dip in the Unseen Seer class, while slowing your maneuver progression by 1 IL, allows you to add Hunter's Eye to your spell list, granting +1d6 SA/3CL.

That's if you want to 2WF.

If not, power-attacking is a sensible option, but you also gain access to Diamond Mind. You could easily (very easily, in fact) optimize Concentration checks and take all the Diamond Mind Concentration maneuvers, making you virtually invulnerable to spells (low fort matters no more!) that offer saves AND taking care of your damage.

Then again, Emerald Razor Power Attacking is probably the easiest damaging tactic to come online.

No more than 3 levels of Swashbuckler.

In a Daring Outlaw? Rogue3/Swash17 is kinda THE build.

@OP: You may want the standard Barbarian1 dip for Pounce and WhirlFrenzy.

So I have an opportunity to play in a friend's roll20 game. I was asked to take on the skill monkey role and since I've got pretty much the best rolls (18, 17, 16, 14, 8, 17) (I suggested point-buy ), I thought "why not take it into melee as well".

We're starting at 5th level, with standard (9k gp) WBL. That's not a problem - I settled on a Factotum3/Hit-And-Run Exoticist1/Warblade 1 with Iaijutsu Focus. The DM was so kind as to allow my Factotum to trade spellcasting for martial dilettante homebrew (full BAB, 1 maneuver known/readied at 3rd lvl, swappable everyday) ACF.
He also allowed my quick-draw to allow for free-action sheathing of the weapon (I DID point out the possible shenanigans).

Basically, the premise of the character is a wanderer swordsman that got dishonored by disobeying orders in the midst of battle - for a noble cause nonetheless. He's meant to unlock his ancestry and slowly learn the supernatural art of using wind in battle (yeah, I like Yasuo. Don't judge... Too much).

What I'm asking for is the direction in which I should take my build not to overshadow my party, but still get to do the "cool stuff".
Basically, I want to just be there and do stuff, but have the ability to pull out the big guns when we get in a pinch.

Character sheet (not really final): http://www.myth-weavers.com/sheetvie...heetid=1024818

I thought about:
- One to five levels of Iaijutsu Master (Int to AC, Cha to dmg - multiple times, Cha to Initiative)
- Four (or more) levels of Swordsage (Desert Wind/Setting Sun both have some yummy maneuvers)
- Continuing Warblade (Diamond Mind and Iron Heart get some good stuff as well)
- Two or four levels of Bloodstorm Blade (and fluffing the throws as "wind cuts" instead)
- Suel Arcanamach levels, (ab)using Whirling Blade in conjunction with Iaijutsu Focus
- Sorcerer1/Abjurant Champion5, reasons same as above.

I can't quite put my finger on what combination exactly would be the most fitting.

The rest of the team:

Kung-Fu Genius Unarmed Swordsage1/Monk2/Cloistered Cleric 1/Swashbuckler 1 going into Daring Outlaw and Kensai. I helped that player build, but we mostly went with what sounded cool. I know this guy will play decently, but without big surprises.
Sorcerer5 going into Incantatrix. Big unknown to me, I've never seen the player in action. Most probably a straight-up blaster employing Disintegrates (yep).
Warlock 5 - as above. As far as I know, isn't entering Hellfire Warlock.
Cleric 5 - a healbot/support.

As a sidenote, I got told that the sorcerer may not be able to play.

Off the top of my head:

Int-focused
Martial Rogue4/Swashbuckler3/Swordsage2/Martial Rogue+x

Swash3/Invisible Fist Decisive Strike Martial Monk1/Swordsage2/Warblade14
Dex>Con>Int focus, int to damage, int to AC (with Carmendine Monk or Kung-Fu Genius feat),

Cha-focused
Battle Dancer1/Bard4/Swordsage1/Crusader or Warblade 14
CHA to AC, some bard casting. Song of White Raven stacks Bard and Crus/War levels for Inspire Courage. Get Song of the Heart, maybe DFI. Kick butt.

In all cases - Swordsage gives +2d6 sneak attack (Assassin's Stance) and qualifies you for Shadow Blade (Dex to dmg) (or, in first case, for Daring Outlaw).

At level 5? You don't need actual spellcasting to pull off healing. Just make your party chip in for a wand of Lesser Vigor, at 750gp it gives you a return of 500hp. You can use it even with just one level of Paladin.
In-combat healing? Well, unless you get access to Tome of Battle, there's little chance of gaining a meaningful way of doing that.
You could dip Dragon Shaman for Aura of Vigor - free healing up to 50% of maximum health for everyone.

Oor you can just go Cleric5 (buy the wand anyway), and roll with 3rd level spells.

EDIT: Oooh, everything on SRD? Can you ask your DM if online Wizards resources are also allowed?

It seems like it'd be too much. A boss is most of the time a level or two ahead of the party anyway, so with this they could nuke to oblivion if they happen to be a caster.
If you want them to be able to stand their ground in action economy, a more sane option would probably be giving them JUST an additional standard action.
The easiest way is simply adding mooks, though.

Combat Reflexes feat. You gain additional AoOs equal to your DEX mod.

BAB? BAB is easy, since at Wiz1/KP3 you have the requisite +3 BAB. If you somehow are able to gain (even) more feats, the Extra Spell feat, used RAW, enables you to learn Haste as a 1st level spell (Thanks to the Trapsmith). At that point it should be easier to just go Wiz1/EK3/SwB, since you save a feat.

Run with a standard Bardblade or Bardsader (depending if you want more raw damage or some in-combat healing respectively) build with the Song of the White Raven.
Take your first level as a Crusader or Warblade, then go into Bard for two levels, re-enter the first class, go Bard for another two levels, then full-Initiator.
Final build looks like Initiator16/Bard4.
If you focus on optimizing numerical Inspire Courage bonus + the White Raven maneuvers you can easily make your whole party awesome(r).
The Leading The Charge/Leading the Attack maneuvers alone give your party a +4 to hit against the enemy "marked" by you, so you can offset the poor attack rolls a bit.

Okay, I nerfed Pack Tactics a bit. Is it still too much?