Help with a build for a heist game?

[Carrion Knight]

My group is planning to start a 3.5 Waterdeep set thieves guild game soon and I'm stumped how to build my character. I was hoping to play either a dashing swordsman who can act as the party face, or a lookout who can climb, swim, or get anywhere to assist the party after.
We start at level 2 with a restriction that our first level be in a class that gets the hide skill.
I became completely stumped with the lookout build and swordsman seems more plausible. I think perhaps scout for level 1 and then 3 levels of swashbuckler. The high int for skills will help me fight as a swashbuckler, and skirmish might be fun to use, but after that I'm stumped. Being new to the game I'd like to keep this a simple build, not looking to metagame, just to fill my role. If you can help me out with this I'd be greatful.

[Particle_Man]

Well one classic build is to go Rogue 1/Swashbuckler 3/Rogue 2/Swashbuckler forever and at level 6 net the feat Daring Outlaw. This lets you count both rogue and swashbuckler levels to determine sneak attack damage.

If you have a nice DM, maybe something similar could be done with Scout's skirmish instead of Rogue's sneak attack.

[pabelfly]

What combat style would you like to use? Do you want to use a two-handed Greatsword? A pair of short swords for a two-weapon fighting build? Or a sword and shield?

[Carrion Knight]

I was hoping for a rapier in one hand and preferably nothing in the other, but that might not be viable. In any case a musketeer, fencer kind of style.

[pabelfly]

I was hoping for a rapier in one hand and preferably nothing in the other, but that might not be viable. In any case a musketeer, fencer kind of style.

Don't worry, you can do all sorts of stuff in 3.5. Wielding a rapier in one hand is perfectly fine.

My suggestion is straight Swordsage. You'd have 6 + INT skill points each level, which sounds like it's important to you, and the Hide skill. You'll be able to pick from various manoeuvres to boost your damage and give you some options in combat. You can add your Wisdom to your AC while wearing light armor.

I'd suggest picking up Weapon Finesse, so you can use your dexterity stat for attack rolls, rather than STR, and Improved Initiative if you really want to try to get the first strike in.

[Carrion Knight]

I hadn't heard of swordsage before, and being newer to the game the spellcasting makes me nervous. My main concern is that it lacks any charisma skills that could make me a face. Could the rogue or scout at fist level for the skills work with swordsage?

[Eladrinblade]

Sneak-attack Hit&Run Fighter + Swashbuckler + Daring Outlaw + Cosmopolitan (Hide). That's not technically a class with hide, but your DM might allow it. Anyway, rogue is going to be a solid choice no matter what. Maybe consider a lurk, a beguiler, a rogue/mage/arcane trickster, or a swordsage.

[Carrion Knight]

I started reading more into swordsage and it sounds pretty cool so far, if my party doesn't need a face I'll probably go straight swordsage. Is there a way to get skill proficiency without dipping into another class?

[Particle_Man]

Note that if you are set on fighting with one hand and leaving the other free, there is a feat called Deflect Arrows that is a fairly cool one (you simply stop one ranged missile attack per round that would otherwise have hit you). But rule of cool aside, it really depends on whether you will have opponents that try to hit you with ranged attacks.

The Apprentice Feat from DMG II is one way to get some skills as class skills.

[Biggus]

Is there any reason you're avoiding Bard? Seems the obvious choice for the dashing swordsman/party face role. And gets Hide. :elan:

[pabelfly]

Here's a link to a thread on how to get extra class skills:

https://forums.giantitp.com/showthread.php?491181-Alternative-ways-to-get-new-Class-skills

Swordsage comes with Intimidate if you want to persuade people that way. Martial Study (White Raven) can get you Diplomacy if you prefer that instead.

[Carrion Knight]

I'm playing a favored soul in a different game, and with how poorly I memorize spells I'd like to avoid spellcasters. So bard is out I think, and though swordsage has maneuvers I think the limited number won't be that bad.

[Biggus]

So bard is out I think, and though swordsage has maneuvers I think the limited number won't be that bad.

A Swordsage only has slightly less maneuvers and stances known than a Bard has spells known (31 vs 35 at level 20 for example).

Obviously, if you'd rather play a Swordsage, play one, but don't do so because it's much simpler than a Bard, because it isn't.

[Particle_Man]

If you play a sword sage then the feat adaptive style might be useful.

[Particle_Man]

If you want a simpler class than swordsage there is warblade in the same book. Fewer skill points but a nice selection of class skills for a face character. Fewer maneuvers and stances to keep track of. More hp and base attack bonus.

[Maat Mons]

If multiclassing with a skillful class, the Able Learner feat (Races of Destiny, p150) can be very nice. It allows you to buy cross-class skill ranks for one point each instead of two points each. And since your maximum number of skill ranks is set by having at least one level in a class that has that skill as a class skill, in practical terms, Able Learner lets you merge the skill lists of all your classes.