Complete Scoundrel (3.5e Optimized Character Build)
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This isn't a "max out damage" type build. I am personally sick of seeing my favorite expert role reduced to just sneak attacks, and I am really in awe that DMs would allow PCs to pick assassins. This is about being able to deal with any situation the game throws at you whether it be intrigue, breaking into and out of places you should not be, gathering intel, or "ghosting" people. Take advantage of your high skills and tricks to excel (or do over any failures) in all areas of scoundrel-hood. In battle you will be killing nukers, healers, and other support roles as quickly (and quietly) as possible. And of course you will need the ability to get away ASAP when things do go wrong. The goal is to end 20 lvls with +10d6 sneak attack and BAB of +15 or more, which is basically a rogue's ending stats, but the ability to do all the aforementioned things.
This will bare a lot of similarity to the "daring outlaw" build on this page, but with more emphasis on tricks and skills, and is legal (ie lvl 1 warblade using lvl 5 spells and NO assassin).
PH, PH2 (telling blow), complete adventurer (nightsong enforcer), complete warrior (invisible blade, swashbuckler), complete psionics (ardent), XPH (hustle, charm), unearthed arcana, tome of battle (swordsage)
Game Rule Components
Spells, Powers, Soulmelds, Stances, etc...
Must have spells/powers and tricks: Psionic charm, Hustle (extra move action), Assassin stance (+2d6 on sneak attacks), shadow jaunt (shadowstep), child of shadows, group fake out, social recovery, acrobatic backstab, spot weak point, clarity of vision, timely misdirection, shrouded dance (trick version of cloak dance), corner perch, slipping past (remember that uncanny trickster gives you 3 free tricks)
would be nice: moment of perfect mind, mind over body, island of blades, never out numbered or any trick skill that fits your stats
stat boosts take priority, especially for skills you will be using a lot. You will most likely had sets of equipment depending on if anticipate fighting, infiltrating, or for social occasions. In most cases you will not be wearing armor since unfettered defense, AC bonus and grace all say no to armor, you could use psychoactive skins instead with the ultimate goal of getting Skin of iron (DR 15). Rings of protection the best your level/DM allows will almost always be needed. Have a bunch of cognicence crystals as well because you have very low power points and there are times you will want to use hustle more than 2-4 times a day.
For weapons beg, borrow, steal for a set of keen, blurstrike (first attack will make opponents flat-footed) kurki of the best enhancement. Once you get improved critical switch to a holy, blurstrike instead. If you can get parrying traits on them then so much the better.
As with any class that relies on sneak attack and crits for damage you will be vulnerable to undead and constructs. Always invest in a weapon that has holy or undead bane and construct-bane as side arms.
Starting Ability Scores: Dex and INT are your main stats but you will want everything high. Nothing you can't make up for with gear and skill ranks, or just avoid a certain trick till you have enough ranks in it. You will need wisdom of at least 12 to pick Hustle.
Race: human. flaws murky eyed, shakey (take this one when you have +5 BAB)
|Saving Throws||Feats|| Class
|1st||rogue 1||+0||+0||+2||+0||Point Blank Shot, Two-Weapon Fighting, far shot, telling blow, B||sneak attack +1d6, trapfinding|
|2nd||ardent 1||+0||+0||+0||+2||noneB||mantles: Freedom-+10 to move, communication-+2 to diplo Powers: hustle, charm|
|3rd||swordsage 1||+0||+0||+4||+4||Weapon Focus (kukri), psicrytal affinity (+3 concentration or +2 initative)||pick more tiger claw moves since that is your focus|
|4th||swordsage 2||+1||+0||+5||+5||AC bonus|
|5th||swordsage 3||+2||+1||+5||+5||assassin stance (+2d6 sneak attack)|
|6th||invisible blade 1||+3||+1||+7||+5||speed of thought||sneak attack +4d6, unfettered defense|
|7th||invisible blade 2||+4||+1||+8||+5||bleeding wound|
|8th||invisible blade 3||+5||+5||+8||+6||deadly precision, improved initiative||dagger sneak attack +5d6, uncanny feint (move)||ability score increase, take another flaw for said feats|
|9th||uncanny trickster 1||+6/+1||+5||+10||+6||Improved Two-Weapon Fighting||favorite trick, bonus trick|
|10th||uncannyy trickster 2||+6/+1||+5||+11||+6||fient master (add class features of invisible blade0|
|11th||uncanny trickster 3||+7/+2||+6||+10||+6||uncanny feint (swift), dagger sneak attack +6d6|
|12th||nightsong enforcer 1||+8/+3||+6||+12||+6||Improved Critical (kukri)||sneak attack +7d6, teamwork||ability score increase|
|13th||barbarian 1||+9/+4||+8||+12||+6||fast movement, rage|
|14th||barbarian 2||+10/+5||+9||+12||+6||uncanny dodge|
|15th||rogue 2||+11/+6/+1||+9||+13||+7||greater two fighting||evasion|
|16th||rogue 3||+12/+7/+2||+10||+13||+8||trap sense +1, sneak attack +8d6||ability score increase|
|17th||rogue 4||+13/+8/+3||+10||+12||+8||improved uncanny dodge|
|18th||swashbuckler 1||+14/+9/+5||+11||+12||+8||Daring outlaw, Weapon finess (rapier)||sneak attack +9d6|
|19th||swashbuckler 2||+15/+10/+6/+1||+12||+12||+8||grace +1|
|20th||swashbuckler 3||+16/+11/+7/+4||+12||+13||+9||insightful attack, sneak attack +10d6||ability score increase|
Get into trouble, get rid of trouble, spot trouble, get out of trouble. There should be nothing you can't handle.
The dip into ardent gives you the best ability for fighting and interacting, open up psionic feats and give you a psicystal which you can use as a scout once you get shared sight. Psicystal affinity is like 2 feats rolled into one (alertness and whatever personality you pick) and it gets even better with time.
Hustle will let you move then make a full round action, or it could double you movement and work like spring attack. This power is just too good to pass up, get an love it.
If you are psionically focused (always have at least one point left over), at lvl 13 you have 60 feet of movement, from freedom mantle, speed of thought and fast movment. (or 70 if you use boots of striding). This means you can move silently at a rate of 30 feet or you could hustle and move 60 feet at normal speed. With boots of striding this get even more silly. Use timely misdirection to offset any attacks of opportunity.
Spot weakness is a great trick to deal with heavily armored brawlers and should be made into a favorite. It resolves the next attack as touch attack with a successful spot check (DC= targets AC), spot should be max'd anyway since you are the group expert/scout and alterness feat granted by your psicystal will give a healthy boost.
Charm will allow you to make the most of every interaction, hopefully your DM will be reasonable and let you add your CHR modifier on the DC, otherwise you will need psimatricies or ioun stones to increase the it. The mantle will also let you have +2 on diplomacy and reduce the "speedy diplo" penalty to -5 instead of -10. All social checks should start with charm, then a diplomacy check. If it fails uses second impressions to reroll the result. It is highly unlikely that all three of them would fail (espcially if you capped all of them), especially against 0 lvl NPC when you are gathering info, talking your way into an exclusive party, or flirting your way into a hussy's pants, or convincing a foe that you really have his/her best interests at hand.
Swordsage will give you +2d6 on sneak attacks, the ability to use concentration checks in place of any check (works even better if you picked single-minded for psicrystal), shadow step, and gain concealment by moving. Since you picked tiger claw as your primary you to have (to get the weapon focus on kurki) you need a bunch of filler swordspells to make it work. I'll leave that up to you, some of them are pretty decent. Swordsage also has a lot of skills to help keep key skills capped. The diamond mind has spells that let you use a concentration check in place of a will, fort, or reflex save. Combined with the +3 concentration from your psicrystal you have no fear of saving throws. Shadow jaunt lets you make fast getaways, or allow you to get into striking position without worrying about attacks of opportunity.
Uncanny feint and group fake out will let you make a bunch of people flat footed at the same time as a swift action partially bypassing the errata.
Uncanny trickster lets you add class features to any existing class you had, and gives you more uses of favorite tricks and more tricks free of charge. At +8 (+ INT mod) it will be a great boon to whatever skill you have been lacking in. If you have a nice DM you could ask him to allow you to use uncanny trickster past lvl 3, and forget about everything past lvl 11. But the best thing about uncanny trickster is that it "gestalts" your character at lvl 2-3 saving you those two lvls of xp.
Teamwork is an underrated class ability since it allows you to 'legal metagame". The +1d6 to sneak attack is welcome though.
The build technically ends at 12, I only went with 2 of barbarian and 4 rogue since I wanted improved uncanny dodge, but you could just as easily went all rogue at get massive amounts of skills. Swashbuckler was mainly for the BAB at to sneak in more defense.
If you take out speed of thought and deadly precision, you could take psionic weapon and deep impact instead, since spot weakness might not be as effective. In which case you will want to retrain swift concentration as a favorite trick instead.
Another way to do it is go rogue 5 and lurk 3 and take lurk mastery as you last feat. Lurk uses INT as it main stat so you could get a nice bump in power points, and in 3 lvls you have the potential deal 3d6 more sneak attack or stun with it. OR if you are really daring you can take lurk all the way to 20. This add INT mod to your initiative, potential +6d6 to your sneak attack, 8 sneaky powers, ignore concealment (which nulls murky eyed), flat flat opponent at will, all at the cost of 2 power points each. The main drawback of lurk to this build is the lack of skill ranks.
The truedeath weapon augment crystal from Magic Item Compendium allows the character to sneak attack undead with no minuses to attack or damage.
combat pretty plays out the same as the daring outlaw build, but less consistent due to lower BAB. You could check that out to get the gory details.
With the right equipment this build can handle anything within 5 lvls of his CR assuming the target doesn't have the opposed skills. Anything over that increases the risk that his skill and tricks will fail him, but that is what hustle, shadow jaunt, and a lot of speed are good for.
Undead and constructs are immune to sneak attacks, crit hits, and charm. All of them are your bread and butter. Even with the proper bane equipment, this build is still reliant on sneak attacks and crits, not being able to do that reduces them form optimal to just useful.
Not sure Swordsage can pick up Assassin stance at 3rd level as listed. Nightsong enforcer requires evasion as a prereq.
@1st and 8th levels: Re-reading UA, it looks like each flaw only gives you 1 feat, not 2.