Help me build a rogue type with gypsy flavor.

[TLO3]

My character is from a gypsy clan and I want to roll my character to fit the theme. I'd thought hexblade for the cursing, but it's a little too limited.

The other party members are druid, paladin, and archivist so I'm thinking maybe going the skill monkey route.

Read through the rogue handbooks and I have a starting concept.

Rogue/swashbuckler seems like a fun start. Maybe going with invisible blade or dervish later. I have a decent stat array. 18 16 14 13 11 9 or 17 16 15 12 11 10. Starting at level 5 and has to be human or a halfbreed.  Would also consider going arcane trickster, but don't want to spread myself too thin.

I've never played anything with less than d8 hitpoints so with those classes what should I be looking at for fighting style? Spring attack sounds safer, but I'd only be getting one hit off. I like the dervish idea, but is there any way to get sneak attack on anything past your first hit? If I go Invisible Blade with it, all those extra attacks will only be with daggers so is it even worth it? Also, am I gimping my skills too much by taking too many 4 + Int classes?

Feats will be tough. I'm human, but no flaws are allowed and if I'm the skill monkey, I'll need Able Learner for one of my first slots. Can anyone give me some advice on what levels and feats to take and the best way to take advantage of this guy in combat?

I have access to any book, but my DM has a low cheese tolerance so keep that in mind please. I'd prefer keeping a consistent class flavor as well.
Thanks

Edit:

[RobbyPants]

Rogue/swashbuckler seems like a fun start. Maybe going with invisible blade or dervish later. I have a decent stat array. 18 16 14 13 11 9 or 17 16 15 12 11 10. Starting at level 5 and has to be human or a halfbreed.  Would also consider going arcane trickster, but don't want to spread myself too thin.

I made a character similar to this once and had a lot of fun.  I'd recommend Rogue 4/Swashbuckler 1 for 5th level, and put all other levels into Swashbuckler.

As for stats, I might do something like Str 11, Dex 18, Con 14, Int 16, Wis 9, Cha 13, but they could be moved around a bit.

I've never played anything with less than d8 hitpoints so with those classes what should I be looking at for fighting style? Spring attack sounds safer, but I'd only be getting one hit off. I like the dervish idea, but is there any way to get sneak attack on anything past your first hit? If I go Invisible Blade with it, all those extra attacks will only be with daggers so is it even worth it? Also, am I gimping my skills too much by taking too many 4 + Int classes?

If you want to max out your Sneak Attack damage, take the Daring Outlaw feat (Complete Scoundrel) at 6th level.  That lets you stack Rogue and Swashbuckler levels for Sneak Attack, so a 4th level Rogue/5th level Swashbuckler gets 5d6 Sneak Attack like a 9th level Rogue. 

You can get Sneak Attack on any hits that qualify.  Flanking is the most reliable way to be able to full attack and get multiple Sneak Attacks.  Taking Two Weapon Fighting is also very important to get more attacks in.  If you get access to the Grease spell (through a wand and Use Magic Device), you can use Grease to sneak attack most creatures.

The trick I used with my PC was to get a wand of sculpted Grease (2nd level spell with the metamagic feat) put in a wand chamber (Dungeonscape) in one of my short swords, so I didn't have to draw it out.  By sculpting it, you get a much bigger area, and it lasts for 3 rounds because it's a 2nd level spell.

Feats will be tough. I'm human, but no flaws are allowed and if I'm the skill monkey, I'll need Able Learner for one of my first slots. Can anyone give me some advice on what levels and feats to take and the best way to take advantage of this guy in combat?

The feats I took with my PC (played levels 7 through 9) were:

L1: Two Weapon Fighting
Human: Able Learner
Swash 1: Weapon Finesse
L3: Quick Draw
L6: Daring Outlaw
L9: Improved Two Weapon Fighting

[Bozwevial]

RobbyPants: Swashbuckler is nice--for three levels. Even with Daring Outlaw, it's a little underwhelming.

TLO3: If you're going into dervish, don't take Spring Attack. It's not really worth it and eats feats. If you have a high AC/high HP, Karmic Strike is nice--Mobility will cancel the AC penalty, so you don't have to tumble if you don't want to.

I'd recommend going dervish, taking Two-Weapon Fighting and then buying Gloves of the Balanced Hand (MiC) which will give you Improved TWF. Your limited feat slots will probably make Greater TWF out of the question.

A dip into swordsage for the Island of Blades stance will solve your sneak attacking problems.

Your build might look something like:
Rogue 3/Swashbuckler 3/Swordsage 1 (not necessarily in that order), and then entry into dervish.
Feats:
Human: Dodge
1: Mobility
3: Weapon Focus (some slashing)
6: Combat Expertise
9: TWF
Swashbuckler: Weapon Finesse
Pick up the Gloves of the Balanced Hand as soon as you can. They'll grant you TWF until you take it at 9th level, at which point they improve to Imp. TWF.

If you want to consolidate attack and damage into one stat and can live without Insightful Strike, you could always take Shadow Blade (ToB) and fight with shortswords, then cut two levels of swashbuckler out of the build. You'll have to enter dervish later, but you'll have more sneak attack dice, Dex to damage, and uncanny dodge. (Rogue 6/Swashbuckler 1/Swordsage 1)

[TLO3]

Thanks for the tips.  Good advice there.

I know I said I have access to all books but with Tome of Battle, I kind of doubt my GM will go for it, especially as a 1 level dip to pick up all those maneuvers.

I'd like to avoid single level dips in anything exotic personally, anyway.  It makes my character feel a bit more... unfocused i guess.

I'll need high Int and Dex anyway, so I think I can live without Dex to damage unless it can be gotten some other way.

With Mobility, I'll probably be able to avoid issues getting into flanking position, but having to move after each attack for dervish dance would hurt that I guess.  Any ideas on how to get Sneak Attacks off for all the hits in a dervish dance?   I'm not sure I understand how grease would help much at medium levels.  A DC 12 reflex save doesn't sound like a very reliable way to ensure sneak attacks, and with the dervish dance I wouldn't have many free squares to move around the guy since you can't return to the same square between attacks.

What about Invisible Blade levels later for the Int to AC?  I'd need to dual wield kukris so my base damage might be less than using scimitars, but I'd get better defense and feinting as a free action which is nice for sneak attacking a vampiric touch or something similar if not for full attacks.

[Bozwevial]

Invisible Blade has been errataed--feinting as a free action can only be done once per turn.

[RobbyPants]

Any ideas on how to get Sneak Attacks off for all the hits in a dervish dance?

If you want to do it by flanking, there are the Vexing Flanker and Adaptive Flanker feats from PHB II, but I think you need Combat Reflexes as a prereq, so it's a hefty feat investment.  Basically, one gives you a total of +4 to hit while flanking (instead of +2) the other lets you use other near-by squared to flank, meaning you don't have to be exactly on the opposite side of as your ally (meaning you can dance around in several squares and be flanking in each one).  Still, I'm not sure it's worth three feats...

I'm not sure I understand how grease would help much at medium levels.  A DC 12 reflex save doesn't sound like a very reliable way to ensure sneak attacks, and with the dervish dance I wouldn't have many free squares to move around the guy since you can't return to the same square between attacks.

The trick isn't in the Reflex save (which I'd actually prefer the target succeed), but in the Balance check.  The magical wording is hidden in the text of the Balance skill.  When balancing, if you don't have at least 5 ranks in Balance (which most monsters don't, even high level ones), you're considered flat-footed (i.e. denided Dex bonus to AC).  Thus, anyone with less than 5 ranks in Balance who rolls a Balance check on your grease can be Sneak Attacked.

Of course, things that fly or are incoporal will avoid this.  Other things can get around it too.  And of course, if you can't Sneak Attack the target, then greasing it won't help you too much either.

[TLO3]

Invisible Blade has been errataed--feinting as a free action can only be done once per turn.

Yeah, that's why I'd say it's useful for sneaking touch attacks but not for multiple melee attacks.  Also, since I'm not going to be wearing much armor, I think I'll need all the AC I can get.  That said, I'll probably want to progress dervish as quickly as possible for offense and may not even see those last levels of IB.

@RobbyPants: Ah.  I forgot that simply performing the act of balancing leaves unskilled creatures flatfooted.

I'm starting to wonder whether rogue is a good lead-in to Dervish.  I'll only get 2d6 SA and mediocre skills for most of my levels.  If I'm going full combat with dervish wouldn't it be preferable to have two fighter or ranger levels instead of the 3 in rogue for easy TWF or feats?  If I'm going skill monkey, shouldn't I get more SA synergy and better skills?  Grrr.  Now I'm torn again.   

If I want to be the skill guy with 4+ Int per level I could take my 18 in Int and max UMD, Tumble, Disable Device, Search, Hide, Move Silently, Bluff, and maybe a few spread out with -3 points for the dervish req.  Ugh.  Plus the 18 in Int means I'm less by one in AC, to hit, and reflex.  Will this be effective enough to fill the skill monkey slot of the party?  I want to be combat effective, but not if it means the party will suffer.

[Bozwevial]

Classic combat-entry into dervish is fighter 2/swashbuckler 3. That said, you should probably go skill-monkey given that your party seems to have combat pinned down pretty well.

For some reason, the factotum comes to mind. I can't think why, but it makes a damn good jack-of-all-trades, and would mix well with the Invisible Blade (terrific Intelligence synergy there).

[RobbyPants]

The scout class (Complete Adventurer) give you trapfinding (so you can be rogue-like in some ways) as well as skirmish.  Skirmish can give you a small boost to damage, but it's triggered by moving at least ten feet per round, so your dervish dance will automatically trigger it.

[TLO3]

Well not sure if I like the factotum flavor, but looking through the dungeonscape I noticed the ACF adds trapfinding and Disable Device as a class skill for ranger at the expense of Track.  I'd start with (6+int) x4 skills, have most rogue skills except for UMD and Tumble(ouch) and get TWF at level 2.

Scout could be good too.  The movement req. on skirmish would have synergy with dervish dance and I'd get +1 AC any time I moved more than 10ft.  Needs 3 levels instead of the 2 of ranger but gets more skills.

I could have 3 Scout/3 Swashbuckler 3 and have +5 BAB, 3 levels of 8+int skills,  1d6 +1 skirmish, +1 initiative, uncanny dodge, trackless step, and +10 movement.  Not bad

With Ranger I'd be 2 Ranger/3 Swashbuckler (can you take a feat to qualify you for a PrC on the level you take that PrC?) with 2 levels of 6+int skills, Favored Enemy, Wild Empathy, TWF and +5 BAB and entry into Dervish at level 6.  If you can't take that feat at the same level then you'd get endurance at level 3 of ranger and then be in at +6 BAB.

Both sound like they might be better than rogue which would have only a 1d6 advantage over scout with less AC and evasion in place of all the extra stuff scouts and rangers get.

Edit: Oof, just remembered that Able Learner is 1st level only.  I'd need 4 levels of scout to qualify for Dervish and 5 or 6 of ranger if I want to keep my CC skills maxed.   4 of scout gets me Combat Expertise as my bonus feat and I lose another point of BAB.  With 6 in ranger I get Improved two weapon fighting, a useless animal companion, useless spells and a 2nd favored enemy.  Could probably dig up some useful ACF for the spells and companion.

2 levels of fighter would get into dervish quicker, but I'd never be a trap finder that way.

[TLO3]

Okay, I see two options I like for the Dervish route.

Scout 4/Swashbuckler 3 - BAB +6, Fort +5 Ref +5 Will +2  8 more skillpoints than ranger build

1 Sct 1: Skirmish (1d6), trapfinding, Able Learner, dodge
2 Sws 1: Weapon Finesse
3 Sws 2: Grace +1, Mobility
4 Sws 3: Insightful strike
5 Sct 2: Battle Fortitude +1 (initiative bonus), uncanny dodge
6 Sct 3: Fast Movement +10, Skirmish (1d6, +1 AC), Trackless Step, Weapon Focus (Scimitar)
7 Sct 4: Bonus Feat- Combat Expertise

Ranger 4/ Swashbuckler 3 - BAB +7, Fort +8 Ref +5 Will +2

1 Rng 1: ACF: Arcane Hunter, ACF: Trap Expert, Wild Empathy, Able Learner, Dodge
2 Sws 1: Weapon Finesse
3 Sws 2: Grace +1, Mobility
4 Sws 3: Insightful strike
5 Rng 2: Combat Style - Two Weapon Fighting
6 Rng 3: Endurance, Weapon Focus (Scimitar)
7 Rng 4: ACF: Champion of the Wild (Combat Expertise), ACF Distracting Attack

Going scout gives some good battle bonuses like faster movement, higher AC and higher initiative while ranger gives higher BAB and a head start on TWF.   I think that's as good as I could get for a dervish build that still can function as the party's detrapper.

I've strayed quite a bit from my initial concept of combining a high int for rogue with insightful strike and running from there.  I'd like to think about some options other than Dervish and more geared towards a combat rogue.  Is SWS 3/Rogue 17 worth bothering with?  I could throw the Swift Ambusher in so I'd get grace and dodge bonus levels (meh).  I wanted more Int synergy which is why I was toying with Invisible Blade initially, but I have no idea how combat effective that would turn out.  Any other build suggestions?

[Psychic Robot]

Question: What do you want your build to do mechanically?

Rogue 20 works just fine; "gypsy flavor" is not a rules thing, unless you are looking for something mechanical that you feel is "gypsy-like."  For instance, if you wanted to go the "divination" route, I'd suggest combining rogue, sorcerer, and unseen seer levels--but I don't know what you want.

[TLO3]

I wanted a nomadic flavor to my character.

It's funny that you mentioned the Unseen Seer route because that's kind of what I've decided on after deliberating on it more.  I'm planning on starting 1 Rogue/4 Diviner and then start taking US levels.  I'm missing out on that 5th level bonus feat, but it's probably going to be a lowish level game so I'd rather get into US as soon as possible.

Current plan is:

9 Str, 16 Dex, 14 Con, 18 Int, 11 Wis, 13 Cha

1 Rogue: Able Learner, Craven
1 Diviner: Improved Initiative (ACF Fighter bonus feat for scribe scroll and wizard feats), lose Evocation school
2 Diviner: Practiced Spellcaster
3 Diviner: +1 Int
4 Diviner:x

Then into unseen seer.

[RobbyPants]

That certainly seems resonable.  It's up to you if you want to take one more level for that metamagic feat at Diviner 5.  Of course, your BAB and saves will not progress at that level, so you're certainly paying for the feat.

[Irthos Levethix]

If you go the Unseen Seer route, you might want to look at some of the ACF's in Unearthed Arcana.  I'm not sure whats available for the Diviner, or if they're even any good, but it might be worth looking at before you totally shrug off that 5th level bonus feat.

[Shadowhunter]

There is a great ACF if you are going Diviner Route.

Spontaneous Divnation, p.52, Complete Champion.

Lets you spont. cast any divination spell by using up a prepared spell of the same level or higher.
You'll gain it instead of your 5th/10th/15th/20th level bonus feat.

[RobbyPants]

If you go the Unseen Seer route, you might want to look at some of the ACF's in Unearthed Arcana.  I'm not sure whats available for the Diviner, or if they're even any good, but it might be worth looking at before you totally shrug off that 5th level bonus feat.

I looked at the ACFs in UA and none of them jumped out at me.  The only one that would maybe be worth it is where your bonus feats come from a different list, although I don't remember offhand if you can swap it out for Scrive Scroll at level one. 

There are also some things you can get if you drop your familiar, but it's things like IDing objects in 10 minutes instead of an hour, double speed on Arcane Eye, and +1 DC on your divination saves.  I don't think it's worth dropping a familiar.

[Phaxi]

I wanted a nomadic flavor to my character.

It's funny that you mentioned the Unseen Seer route because that's kind of what I've decided on after deliberating on it more.  I'm planning on starting 1 Rogue/4 Diviner and then start taking US levels.  I'm missing out on that 5th level bonus feat, but it's probably going to be a lowish level game so I'd rather get into US as soon as possible.

Current plan is:

9 Str, 16 Dex, 14 Con, 18 Int, 11 Wis, 13 Cha

1 Rogue: Able Learner, Craven
1 Diviner: Improved Initiative (ACF Fighter bonus feat for scribe scroll and wizard feats), lose Evocation school
2 Diviner: Practiced Spellcaster
3 Diviner: +1 Int
4 Diviner:x

Then into unseen seer.

Another option is to go Spellthief instead of rogue. Then together with Master Spellthief and use Hunter's Eye (ranger 2, PHB2) as bonus spell from Unseen seer bump your sneak attack to awesomeness.

[j0lt]

I'm seeing a lot of TWF suggestions for this rogue's 3/4 base attack.   :-\

As a counter, I'd say use STR as your dump stat; build a charismatic rogue armed primarily with a shortbow.  You don't want to be in melee range with that d6 hit die.
For your stats, I'd recommend: 10 17 12 16 11 15, raising Dex to 18 at 4 and Cha to 16 at 8.

If you really want to be more of a blade user, combining Invisible Blade with Master Thrower makes for a dagger-throwing nightmare.  (really great, as long as your opponent doesn't have DR)
Recommended stat spread: 14 18 13 16 11 9 (or swapping str and con)

[woodenbandman]

Rogue special abilities >>>>> Grace. Take Savvy rogue, at least 10 levels of Rogue, and pick up Kusari-Gama Proficiency and the Opportunist special ability. Combat Reflexes is also needed. Oh, and the TWF tree. Also, Crippling Strike is nice, as is skill monkey... er, mastery.

Daring Outlaw's fine and dandy for what it is, but its main purpose is(to my knowledge) acheiving reasonable damage while you're not sneak attacking, and if you're not, then why are you playing a rogue? Max levels of Swashbuckler are 3, in my opinion. I do love the concept, and it would be much better for something like Ranger (which, I believe, exists, though I could be thinking of Scout). If you take 16 levels of Rogue, 3 levels of Swashbuckler, you've got one left over, which I'd fill up with something that has a d10+ hit die and a high BAB, or you could pick up a level of Ninja if you have a high wisdom for some uses of Invisibility per day to help you get into flanking position/sneak attack targets that are looking directly at you/etc. Although I hear that a great deal of things see invisibility at 20th level.