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Essentials Swashbuckling Slayer

A flexible DM would let you swap out Stealth and Thievery as the automatic skills and plug in Streetwise and Diplomacy, given your description: "He's urbane and will spend his down time in some city tavern drinking, carousing, and wooing the ladies with tales of his exploits." He's a worldly sort, so it makes sense to spend the other skill slots on Perception, Insight and the Fighter-y stuff.

If you don't like the flavor of Backstab and Sneak Attack... Well, maybe you could get Power Strike instead of Backstab, but the fact is that the Thief has two real core traits: Sneak Attack plus skills and skill bonuses. Without SA, it's not a Thief. With SA, it's not really your concept.
Or just change the name Sneak Attack to Precise Attack.
 

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If you don't like the idea of losing so much damage output from wielding a rapier, you could just slot a greatsword or a fullblade and call it a rapier anyway. Refluffing is wonderful stuff.

You could even use a bastard sword for maximum flexibility; one hand free for grabbing and stunts, or "two handed swing" for class features and damage via the versatile property. Does it matter if your "two handed grip" actually involves fighting with your offhand behind you for balance?

Yes, then you are technically using a heavy blade, but Heavy Blade expertise gives you a +2 vs OAs (which, given your description, you will probably be provoking from time to time), and lets you make full use of your class features.

You could also use a spiked chain and call it a rapier. It has reach (lunging fencing-style strikes) and is still a light blade for the feat support, though I don't think it helps you for class features.

I know some people don't like refluffing, and some DMs may take exception to extreme refluffs such as this, but it is food for thought nonetheless.

I love the flexibility of the Slayer for things like this. High Dex, Melee Training, and Light Armour; great combination. You still get much of the damage output and will have even better AC if you go Hide (again, refluff as desired) and start with 20 Dex.

You might even MC swordmage for the lovely once per day Warding that will boost your AC even further for that really tough fight.

Good luck and happy swashbuckling!
 

A flexible DM would let you swap out Stealth and Thievery as the automatic skills and plug in Streetwise and Diplomacy, given your description: "He's urbane and will spend his down time in some city tavern drinking, carousing, and wooing the ladies with tales of his exploits." He's a worldly sort, so it makes sense to spend the other skill slots on Perception, Insight and the Fighter-y stuff.

If you don't like the flavor of Backstab and Sneak Attack... Well, maybe you could get Power Strike instead of Backstab, but the fact is that the Thief has two real core traits: Sneak Attack plus skills and skill bonuses. Without SA, it's not a Thief. With SA, it's not really your concept.

Yes yes on the swap the skills.

Or just change the name Sneak Attack to Precise Attack.

BINGO ... And then, a minor re-badge of sneak attack and backstab (thinking essentials theif...they rock) and you have the "precision" style of a rapier fighter. You know..."expose and exploit the weakness" (followed by a witty retort) rather than "Me Mad! Thwak Thwak Thwak!"

It even gives you (a little) support for charisma, further matching the fluff description you gave.

IMHO It just seems much closer flavor wise to what you are trying to achieve, and you will get a bit more "oomph" out of it damage wise.
 


For a rapier wielding rogue, Flash of the Blade allows you to use your sneak attack just by being the only person engaging someone. Seems like a good way to make it less sneaky and more duelist.
 

For a rapier wielding rogue, Flash of the Blade allows you to use your sneak attack just by being the only person engaging someone. Seems like a good way to make it less sneaky and more duelist.

I don't recall the exact wording on either feat, but I seem to remember Cunning Stalker from HotFK being a direct improvement on FotB. I believe it gives you combat advantage when you're the only thing adjacent and FotB just grants you SA.
 

You basically have two options here to get what you want... and both of them have small negative details you'd have to just be okay with. The Dexslayer has a slight game mechanics difficulty (half mod for damage); the Thief has a slight roleplaying difficulty (certain skills auto-granted and a 'class name' that you don't really want). So in either case, you just have to compromise. Be slightly under-powered compared to "standard" slayers, or have abilities you really don't want your character to have (even if you never actually use them).

If I was making the choice... I would pick the Thief class package and build the character, but then just take a pencil and draw a line through the words 'Thief', 'Stealth', and 'Thievery' on my character sheet. Just because the game is giving me these three things (a class identity, and two automatic skills) doesn't mean I need to accept them. But in every other facet, the Thief class would give me what I wanted.
This statement is not completely true:

while a str 20, dex 16 slayer has +8 stat mod damage, a dex 20, str 16 Slayer has exactly the same stat mod to damage, for the coast of a feat, as using half mod for damage is optional, not mandatory, just a confirmed bug in the CB.

However he has better AC, better ranged capabilities and can be sure to hit the requirements for light blades.

It is only going dex only and spreading other stats around that makes you have less damage than the pure strength/dex slayer. You don´t sacrifice more than a feat and you can hardly call +1 AC and +2/+2 on ranged attacks exactly wasted.
 


Bolded the important part!

Melee Training


Benefit: Choose an ability other than Strength. When you make a melee basic attack using a weapon with which you have proficiency, you can use the chosen ability instead of Strength for the attack roll. In addition, you can use half of that ability’s modifier, instead of your Strength modifier, for the damage roll.
 

I entirely misread that other post. I thought you were saying that halving the modifier was optional, not using the half modifier in place of strength. Apologies for the misunderstanding.
 

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