Optimizing a rogue/swashbuckler/druid for stealth and infiltration

Question

I'm up to level 6 in a friend's campaign with this Rogue 3/Swashbuckler 3. I'm not sure which route to take from here, as there are so many.

For my goal, I'd like to focus on being a super sneaky rogue that no one suspects. I took Changeling for the Incognito mode. I have high bluff and diplomacy for interactions.

After this I plan to go druid until I get a few shapeshiftings/day.

I would like to keep a balance leaning toward roleplaying options without completely degrading combat ability. I in a sense want to play my character something like this (not sure if the mechanics will work ...yet):

• For thieving: Changling to get into a mansion disguised as a servant or relative and case the place; wait till no one is looking, or purposely wait till they're looking; grab all the nice shiny things; then trolololo it druid style out the window.

• For combat: Rogue/swashbuckler it up until I'm in trouble, then shift bird and rain down whatever spells my low Wis and +Wis items will give me.

Also among my resources: the DM is allowing me to take 2 flaws for 2 feats. I'm thinking Daring Outlaw for one... not sure about the other.

I am also considering Anklets of Translocation and better armor as things to spend my wealth on.

This is a 3.5 game that allows pretty much anything, so no real restrictions on books. I'd like to keep true neutral as my alignment, but I'll shift that for a good build suggestion.

Answer 1

After this I plan to go druid until I get a few shapeshiftings/day.

Don't.

Multi-classing is a fine thread to walk on. Unless there are specific synergies to exploit (Rogue/Swashbuckler work quite well together for example), by multi-classing you end with a Jack of all Trades, Master of None.

For example, let's suppose that you actually multi-class R3/S3/D5 as proposed. In 5 (long) levels, you will be ECL 11:

• you will have Wildshape 1/day, and be able to Wildshape into a Small or Medium animal of at most 5 HD, say a Dire Hawk (MMII, p. 76); a CR 11 Forest Sloth (MMII, p. 106) has 147 HP, by comparison, and its 2 Claws (2d4+7) + Bite (2d8+3) deal an average of 31 points of damage...

• you will have 3rd level Druid spells; by comparison a 11th level Druid will have 6th level Druid spells. You get Speak with Plants, the 11th level Druid gets Transport via Plants.

• you will make +2d6 (Sneak Attack) and +3 (Insightful Strike) precision damage (average +10) when you catch your opponent unaware, or flank it; by comparison a Rogue 8/Swashbuckler 3 would deal +2d6 more points of damage (average +7), on top of having Improved Uncanny Dodge.

If your only plan to incorporate the Druid class in your build is only to get some weak spells and wildshape, I urge you to reconsider.

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TL;DR: Check prestige classes that you find cool or like, check they can really do what you wish for (some are traps), and build your character toward them.

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If you need some utility spells (who doesn't?), then invest more thoroughly in Use Magic Device. You have the skill in-class (as a Rogue) and 11 skill points per level given your Intelligence, by next level it could maxed out (at 10 ranks), netting you +12. Activating a wand has a fixed DC of 20, pump up Use Magic Device until you get +19 (rolling 1 is not an automatic failure on skills checks), and you'll be able to use any wand: Wizard's, Cleric's, Druid's, ...

If you worry about escape routes, Anklet of Translocation are indeed a cheap and very useful item for now. You can have several for when you run out of charges. Spider Climb is only 2nd level spell (a full 50 charges wand costs 4,500 gp), and few people think 3D when securing houses; much cheaper than flying.

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Which classes to go from there?

You might consider a dip into Swordsage (Tome of Battle), or otherwise use a feat/item to get access to the useful Shadow Jaunt maneuver (Shadow Hand 2, teleport 50 ft. through shadows as a Standard Action). The Swordsage normally relies on Wisdom (bad fit for your character), but only a couple maneuvers really require it so you can just avoid those.

Similarly, a dip into Cloistered Cleric (just one level) would net you 2 Domains (on top of the Knowledge Domain) and 3+Cha Turn/Rebuke Undead attempts per day on top of the ability to use Cleric Wands without a Use Magic Device check. Now the Domains and Turn/Rebuke Undead attempts are not very useful in and out of themselves to you... but:

• Domains sometimes come with passive abilities, such as free feats
• Domains can be converted into Devotion feats (Complete Champion), and notably the Knowledge Domain can be converted into the Knowledge Devotion feat: +1 to +5 Insight on ALL attack rolls and ALL damage rolls, based on a Knowledge check (+5 requires a 36+...) as well as adding one Knowledge skill to your in-class skills (forever)
• Turn/Rebuke Undead attempts can be used to power feats, for example Travel Devotion is 1/day, but you can exchange 2 Turn/Rebuke Undead attempts against another use... as long as have remaining attempts

For example, you could dip Cloistered Cleric with the Knowledge, Travel and Trickery domains, and convert all those into Knowledge/Travel/Trickery Devotion (the latter allow, 1/day, creating a simulacrum of yourself, which gets more and more real as your ECL rises).

Also, check out Complete Scoundrel: the skill tricks inside are "mini-feats" that you can buy using skill points (which you have aplenty). A trick is usable only once per encounter (in general) and you can only have ECL/2 tricks, but picking a couple is quite handy.

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But... personally, I tend to build my characters backward: start from a Prestige class I like, and check how to get the requirements to attain it.

For example, in the infiltrator theme, have you heard of the Nightsong Infiltrator class (Complete Adventurer, p. 62)? Not only do YOU get better at infiltrating, but you also grant bonuses to your teammates (Teamwork Infiltration (Ex), study "obstacle" and grant +2 to allies to bypass it).

Or maybe you'd rather be a Spymaster (Complete Adventurer, p. 77) or a Thief-Acrobat (Complete Adventurer, p. 83)?

Unfortunately, none of those are exactly potent in combat situations; I fear. Infiltrators generally are not.

Tome of Battle has two potential Prestige classes that you might be interested in:

• Jade Phoenix Mage (dip 1 level in Swordsage and 1 level in Wizard + take the Precocious Apprentice feat to get access) is a fighter/wizard gish; only 1 dead spellcasting level, Full BAB, and a spattering of maneuvers and stances.

• Shadow Sun Ninja (requires Good alignment) (dip 1 level in Swordsage to get access; the unarmed variant) is a monk on steroids; it gains extra Shadow Hand and Setting Sun maneuvers as well as abilities thematically based on Light/Darkness.

Initiators are multi-class friendly because your 6 levels of Rogue/Swashbuckler count for 3 Initiator levels (half your levels), so that when you dip Swordsage 1, you count as being Initiator level 4 already (having immediate access to 2nd level maneuvers), and by the end of the JPM or Shadow Sun Ninja (10 levels each), you'll be Initiator 14 (having access to 7th level maneuvers).

I would personally recommend the Jade Phoenix Mage here. Whilst not specifically an infiltrator, at level 18, you'll have access to 5th level spells "for free". There are many spells in the Sorcerer/Wizard list, and you can pick many to help with infiltration (Divination and Abjuration to counter/dispel magical defenses, Transmutation to emulate Wildshape, ...); the Wizard synergizes well with your high Intelligence, and you can have as many spells as you wish in your spellbook.

And yes, you get those "for free" because you will also have a BAB of +15, 11 maneuvers and 3 stances. Plus the capstone is a very cool ability where 1/week you explode (20d6 damage in 20 ft. radius) and 1d6 rounds later reform, dazed but fully healed of all damages :)

Answer 2

The pieces you're interested in for this character are... incongruous. The game does not offer a lot of ways to make them work, but without them question becomes very broad in scope and loses its novelty. That said, I have a very definite sense of how I would like to proceed if I were meant to start playing an interpretation of your concept, so I hope you'll forgive me for offering this narrow and completely dictatorial path ahead:

Chameleon for the spells, Geomancer for the weird.

Since your DM is offering feats for flaws, which are ordinary only selected at level 1, I'm going to take it for granted that he wouldn't mind you taking a level-1-only feat (called Able Learner, by the way) so that you can enter the ne plus ultra of the "I'm level 6 and I don't know what I want" prestige classes. Printed in Races of Destiny and also linked above, the Chameleon class bootstraps an uncertain character like yours into a broad suite of competencies. It's solid stuff. Maybe not always stellar, but that's what you get for not planning ahead. Anyway, the most compelling Chameleon feature, for me, is casting off anybody's list and starting with second-level spells right from the outset, so you're not quite as far behind on level-appropriate abilities. There's also a floating bonus feat and turn undead and stuff. I know the class description says that you need to be human or doppleganger, but a changeling is both of those things and it pretty much says as much in the "Adaptation" section near the end of the class entry.

The Geomancer class, from Complete Divine, is, frankly, a mess. It requires both divine and arcane spellcasting and gradually merges the better qualities of the two, except it only advances one spellcasting class at a time? And also turns you into a mutant because you love the planet so much? I don't know. Look, here's the skinny: on that first point we are all good, because the Chameleon covers both types of spellcasting and is the only class we care to advance. If you can convince your DM to award you benefits that are unenumerated in the description of the Geomancer's Spell Versatility feature, that's great, but at minimum it lets you cast arcane spells in armor and use whichever mental stat you favor for DCs. What made me think of Geomancer at all, though, is the potential interaction between his mutations (called "drift") and your nature as a changeling. Ideally what you do here (and yes I know this is banking on a modicum of homebrew) is persuade your DM to let drift function less as selection of permanent features and more like a menu or set of guidelines for the shapes and functions you can achieve with your racial ability to Changeshape, and thus, the categories of disguise you can assume. The caps on size and absolute utility would be far less than wildshape, but mix-and-match is attractive and you wouldn't be completely tanking your character in the meantime.

Alternatively:

If you like the idea of picking up spells but want to back off of the shapechanging to stick closer to your roots as a sneak attacker, you could go in for Arcane Trickster, a combined spellcasting/sneak-attack classes. Fairly self-explanatory. Note that even though he requires arcane spellcasting to enter, the class actually advances any type of spellcasting you want, so it works fine with Chameleon as its base.

If your DM was willing, you might consider converting your rogue levels into the psionic version. You'll drop a sneak attack die compared to an ordinary rogue, but pick up intelligence-based manifesting to get a handful of subtle supernatural abilities, which are humble, but befitting of an infiltrator. Otherwise you continue on taking same as ever, and take rogue levels for the rest of your life plus the Daring Outlaw feat at level 7.

Answer 3

It sounds like your motive for being a druid is to be able to avoid detection by shapeshifting. That's a good effect, but you're spending five character levels on it, and that's a lot of character levels. (And there's nothing in your background about actually liking nature, which is important for a druid.)

Instead of being a druid, consider using potions or scrolls (of fly and invisibility) to let you avoid detection. This lets you continue leveling as rogue or swashbuckler which will let you keep improving your skills and your sneak attack.

Alternatively consider leveling as wizard, which will eventually let you cast those spells yourself. Wizard is a better fit for your stats since you have high intelligence.

The prestige class arcane trickster is a combination of rogue and wizard; it lets you improve your skills and your spellcasting at the same time. It's a good fit for your character if you go the wizard route.

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Be a little careful, though. The problem with "thief" style characters is that a thieving scene is a conversation between you and the DM, where the other players can't do anything because their characters aren't there. If you do thieving scenes too often, the other players might get bored, or the DM might be reluctant to give your thieving as much attention as you want.