So, thank you to the several players who have complimented or encouraged me to try. Between that and the fact that Katina seems like the sort of DM you don't want to waste (encouraged to see a custom setting someone has been thought into, and point buy rather than "rolling"), I'll try it.
Might be a stupid question - but I'm assuming multiclass XP penalties are N/A in gestalt?
Here is a current draft for a gestalt rogue+fighter / swashbuckler.
Party roles I hope she can help on:
-Partial 'face' char (bluff and sense motive, but not diplomacy)
-Partial scout (stealth and darkvision, but not spot/listen of her own)
-area spell martyr (for Evasion-able things)
In combat she will try to help others by backstabbing things that attack them (or preferably before) and be rather dependent on getting sneak attack conditions, so any tank who can flank with her, or anyone who can cast (Improved!) Invisibility on her, will be a friend indeed. Likewise general buffs (Prot. Evil, Barkskin, etc. and especially Cat's Grace and Bless Weapon since her current gear is light on the 'obvious' bonus types.
If we are doing 'organization building' play, something like teaching at a fencing training school, or being an 'agent' for an organization (like the Harpers in Forgotten Realms), might be an appropriate.
Design parameters as understood: gestalt, L10, standard wealth (49K), 36 point buy, max hp
lesser tiefling, gestalt rogue 6 fighter 4 / swashbuckler 10
Medium Outsider (native)
Hit Dice: 10d10+10 (110 hp)
Speed: 30 ft.
Armor Class: 27 (+5 Dex, +6 armor, +2 shield, +4 dodge), touch 19, flat-footed 22
Base Attack/Grapple: +10/+12
Attack: +1 kukri +19 melee (1d4+9/15-20) or +1 comp longbow +16 ranged (1d8+3/x3) or throwing axe +17 ranged (1d4+6)
Full Attack: +1 kukri +17/+13 melee (1d4+9/15-20) and +1 kukri +17/+13 melee (1d4+8/15-20); or +1 comp. longbow +16/+11 ranged (1d8+3/x3); or throwing axes +15/+10 ranged (1d4+6) and +15/+10 ranged (1d4+5)
Space/Reach: 5 ft./5 ft.
Special Attacks: improved flanking, insightful strike, lesser darkness 1/day, sneak attack 8d6
Special Qualities: acrobatic charge, darkvision 60', dodge bonus +4, evasion, grace +3, resistances (cold, elec, fire 2), trapfinding, trap sense +2, uncanny dodge
Saves: Fort +12, Reflex +15, Will +6
Abilities: Str 14, Dex 20, Con 14, Int 14, Wis 14, Cha 8 [from 36 point buy 14 16 14 14 14 10]
Skills: Bluff 14, Diplomacy 1, Disable Device 17, Disguise 1, Gather Info 1, Jump 9, Hide 22, Move Silently 20, Open Lock 20, Search 15, Sense Motive 13, Sleight of Hand 6, Tumble 17
(Synergies: +2 diplomacy, disguise, gather info, sleight of hand from bluff, +2 balance and jump from tumble, +2 tumble from jump)
Feats: Daring Outlaw, Daring Warrior, Improved Buckler Defense, Improved Critical (kukri), Improved Initiative, Improved Two-Weapon Fighting, Melee Weapon Mastery (slashing), Quick Draw, Sacred Strike, Telling Blow, Two-Weapon Fighting, Weapon Finesse, Weapon Focus (kukri), Weapon Specialization (kukri)
Flaws: Frail (-1hp/level)
Alignment: Lawful Good
Languages: Common, Elven, Infernal, Sylvan
Lesser Darkness (Sp): as darkness except 5' radius and spell level 1st. Caster level 10th (equals character level), 1/day.
Sacred Strike (Ex): sneak attacks against evil creatures deal d8 die instead of d6.
Telling Blow (Ex): critical hits deal sneak attack damage (not multiplied).
two +1 kukris (4,616 gp)
+1 comp longbow (Str +2) (2600 gp)
armor: +2 mithral chain shirt (5100 gp)
shield: +1 darkwood buckler (1,215 gp)
vest: vest (corset!) of resistance +1 (1000 gp)
belt: Belt of Battle: +2 competence bonus to Initiative as a continuous effect. Also has three charges, renewed each day at dawn, which may be used to grant extra actions (1 charge for a move action, 2 for a standard action, and 3 for a full round action). (12,000 gp; from MIC)
boots: boots of speed (12,000)
bracers: Deathstrike Bracers: When activated, deathstrike bracers allow you to use melee weapons to deal extra damage from critical hits and sneak attacks to constructs, elementals, oozes, plants, and undead as if they were not immune to such extra damage. You must still roll a critical threat and confirm it as a critical hit or qualify to deliver sneak attack damage to gain any benefit from the bracers. This effect does not allow you to overcome any other immunity or resistance to extra damage from sneak attacks or critical hits (such as the fortification armor property). This effect lasts for 1 round and may be activated (swift action, mental) three times per day. (5,000 gp; from MIC)
handy haversack (2,000 gp)
efficient quiver, 20 javelins,four mw cold iron kukris, quiver with 400 cold iron arrows and 40 silver arrows, 100 cold iron throwing axes, 10 light hammers, 2 saps, locking gauntlets, grappling hook and 100' of silk rope, thin bedroll and rain tarp, three tendays of rations, flint and tinder, 3 sunrods, two scout's outfits, one silk aristocratic gown, forest camouflage rain cloak (mw tool for hide), soft padded elven footwear (mw tool for move silently; nonmagical base item for boots of speed), mw kits for disable device and open locks, map of the known world, canteen, light warhorse and military saddle
That's a little under 46,000 gp I think; will tally more carefully later
liquid assets: 3,000 gp
Could save 1K per AC point by converting armor or buckler to +1 and adding ring of protection +1 or amulet of natural armor +1, but former is simpler and maybe likely to benefit from allies' buff spells or later loot. Too much of her gear is probably in specialty items, but again I figure she's more likely to be able to loot or commission better replacements or bum buff spells to cover those, so I went heavy on specific / 'wish list' items, hopefully not at too much expense of her AC, saves, and ability scores.
(Empty chakras: head: eyes: amulet: cloak: gloves: ring: ring:)
(Sources: BoEF: Sacred Strike; CS: Daring Outlaw, Daring Warrior; CW: Improved Buckler Defense, Swashbuckler; MIC: belt of battle, deathstrike bracers; Savage Progressions: lesser (LA +) tiefling, PHBII: Telling Blow, Melee Weapon Mastery)