Daring Outlaw (3.5e Optimized Character Build)
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This build is designed maximize damage against creatures subject to critical hits.
Complete Adventurer (nightsong enforcer), Complete Scoundrel (Daring Outlaw), Complete Warrior (swashbuckler, invisible blade), Player's Handbook II (Telling Blow), Tome of Battle (warblade, blood in the water, dancing mongoose, death from above, pouncing charge).
 Game Rule Components
 Spells, Powers, Soulmelds, Stances, etc...
Maneuvers: dancing mongoose, death from above, pouncing charge.
Stance: blood in the water.
|Saving Throws||Feats|| Class
|1st||rogue||+0||+0||+2||+0||Point Blank Shot, Two-Weapon FightingB||sneak attack +1d6, trapfinding|
|3rd||swashbuckler||+2||+3||+2||+0||Weapon Focus (kukri)||grace +1|
|4th||swashbuckler||+3||+3||+3||+1||insightful strike||ability score increase (Dex 16)|
|6th||assassin||+4||+3||+6||+2||Daring Outlaw||death attack, poison use, sneak attack +4d6, spells|
|8th||invisible blade||+6/+1||+5||+8||+2||dagger sneak attack +5d6, unfettered defense||ability score increase (Dex 17)|
|9th||invisible blade||+7/+2||+5||+9||+2||Improved Two-Weapon Fighting||bleeding wound|
|10th||invisible blade||+8/+3||+6||+9||+3||dagger sneak attack +6d6, uncanny feint (move action)|
|11th||invisible blade||+9/+4||+6||+10||+3||feint mastery|
|12th||invisible blade||+10/+5||+6||+10||+3||Improved Critical (kukri)||dagger sneak attack +7d6, uncanny feint (free action)||ability score increase (Dex 18)|
|13th||assassin||+11/+6/+1||+6||+11||+3||+1 save against poison, uncanny dodge|
|14th||assassin||+12/+7/+2||+7||+11||+4||sneak attack +8d6|
|16th||swashbuckler||+14/+9/+4||+8||+11||+4||dodge bonus +1, sneak attack +9d6||ability score increase (Dex 19)|
|17th||warblade||+15/+10/+5||+10||+11||+4||battle clarity (Reflex saves), weapon aptitude, blade magic|
|19th||nightsong enforcer||+17/+12/+7/+2||+11||+14||+5||sneak attack +10d6, teamwork (hear/see allies)|
|20th||swashbuckler||+18/+13/+8/+3||+11||+14||+5||acrobatic charge, sneak attack +11d6||ability score increase (Dex 20)|
Daring Outlaw allows your levels in swashbuckler to stack with your rogue levels to determine your sneak attack damage.
Blood in the water grants a cumulative +1 bonus to attack and damage every time you score a critical hit, Telling Blow allows you to add your sneak attack damage (+11d6) every time you score a critical hit, and the character's threat range is 15–20.
Pouncing charge lets you do a full attack action as part of a charge, and dancing mongoose grants an extra attack with each weapon.
With death from above you can attempt to deal 4d6 points of extra damage with a single attack as a standard action and the opponent is consider flat-footed (sneak attack damage).
Uncanny feint lets you feint as a free action, but it's only usable once per round (as per the Complete Warrior errata). Use the trick skill: group fake out somewhat bypass this restriction.
 Munchkin-Size Me
A possible counter for various undead creatures and their immunity to sneak attacks and critical hits are the weapon abilities ghost strike (Magic Item Comp.) and ghost touch (DMG). They are both +1 enhancement bonuses but to get ghost strike, one would have to get ghost touch on the weapon beforehand because of synergy requirements. Nonetheless, ghost strike allows sneak attack and critical hits to go through normally against the undead.
Other items that may be beneficial to the build include:
- Gloves of Dexterity to increase AC, to hit (Weapon Finesse) , and damage (Shadow Blade)
- Headband of Intelligence to increase AC (Unfettered Defense) and damage (Insightful Strike)
- Ring of Stealth and Cloak of Elvenkind to increase concealment
- Kukris with the Subtlety (+1 Daggers that get an additional +4 when making a Sneak Attack) or Keen (x2 threat range) modifiers
- Other magical items that increase To Hit, Damage, Critical Hit Range, or Sneak Attack Dice when making a Sneak Attack
- Bracers of Defense, Ring of Protection, and Amulet of Natural Armor to increase AC due to the fact that it cannot be raised via Armor or a Shield for Invisible Blades
There is a Forgotten Realms Feat called "Craven" that adds +1 damage to Sneak Attacks per Character Level, but gives you -2 against Fear Saves. Still, the extra damage can be devastating if your DM allows you to take this.
In a similar vein, there is a Dragon Magazine Variant of the Invisible Blade that has Weapon Finesse as a feat requirement rather than Point Blank Shot and Far Shot. As the Swashbuckler is granted this feat for free, this gives the build two additional Feats to make use of if you can take this variant.
 Side Notes
Sneak attack damage only applies to creature subject to critical hits. Keen and improved critical do not stack.
 DM Counters
This build can be modified a number of ways.
- Deadly Precision.
- Power Critical.
- The swordsage class from Tome of Battle has access to "assassin's stance" which increases your sneak attack damage by 2d6. Though you won't be able to use blood in the water with assassin's stance.
- The swordsage additionally has access to the same maneuvers used in this build to which the warblade has access, so they can be swapped. You'll lose one point of base attack bonus in the process.
- Swordsage is also the quickest way to get the feat Shadow Blade, which allows you to apply your dexterity bonus to your weapon damage with select weapons (kukri, unfortunately, is not among the list). However, a rapier is, and with Oversized Two-Weapon-Fighting you can dual-wield them -- while this takes two feats, it can be devastating.
- If you trade two levels of swashbuckler for a level of ronin (Complete Warrior) and a level of spellthief (Complete Adventurer), you can increase your sneak attack damage by another 1d6, at the expense of one feat (ronin requires Exotic Weapon Proficiency [bastard sword]) and one point of base attack bonus.
- Note that these only deal with sneak attack damage. If you're willing to use sudden strike as well, the damage can be increase even further at the expense of your base attack bonus.
- You could also consider taking out the last two levels of Invisible and putting in 3 levels of uncanny trickster instead. Uncanny trickster still give you the class features of invisible blade while allowing you to get a lot more skills and tricks, as well as more uses of tricks like acrobatic backstab (target is flat footed), spot weakness (resolve as touch attack) and swift concentration (if you use any psionics). More importantly it opens up 2 more levels that you could use on other classes, saving you the xp which is usually worth the lose in BAB.
- other way to gain feats in a hurry is to pick up 2 levels in psychic warrior, which comes at the cost of one BAB but lets you get some powers that could make up for it. More importantly it opens up psionic feats, allowing for more flexibility when picking feats (fighter is limited on it own bonus feat list).