Yogah of Yag said:
However, for whatever reason, I don't really associate pirates with assassin-types.
Me neither. If you want to create an assasin type, why not a seaborn thief? Maybe put a level or two of pirate, but make thief your primary class.
Assasin types might look to catch their prey unaware or surprise them so they get little chance to react. For that purpose all the feats that improve initiative are great, although if you are planning to use that on ships where pirates are common, remember they have uncanny dodge, so they are able to defend even when flat footed. Anyway, I would couple a good initiative with brutal attack from Shadizar City of Wickedness, if your strength bonus makes it worth. The feat allows you to triple your strength bonus to damage on opponents you caught flat footed. Again, if the target has uncanny dodge, this wont work, but could make it easier to force a fort save for characters that can't defend while flat footed. If uncanny dodge is being a problem, then feint, but feints are hard to pull if the target has a good sense motive bonus, which is modified by his BAB. You would want to maximize your bluff. The ruffian thief-barbarian multiclass options from Hyboria's Fallen, give you Waiting for the Chance, which after a round of combat spent in total defence, you can make a feint check adding your BAB to it. This is the only way I have found to overcome the sense motive check characters get when feonted in combat.
Then instead of sneak attack you could try poison, and get Poison Use, and feats that allow you to improve your attack bonus, and give you more attacks, thus the target will be forced to make a fort save when hit with a poisoned weapon. The weapon could be ranged. Soldiers have a tough fort save bonus, so if you hit many times, that will force more fort saves, and he might eventually fail one. But if he makes all his fort saves, then you would want to have feats like Run and Fleet footed to get to safety swiftly :lol: You will need access to poison.
For a stangler, take improved grapple and feats that allow you to increase your unarmed damage, and eventually Crushing Grip. If you deal damage with a grapple, you can deal damage to constitution, strength or dexterity. If you reduce your target's constitution to 0, he is dead. The Ruffian gives a god option for grapplesr too: Dirty Grapple, if you succeed at the opposed grapple chek, the opponent is stuned for 1d6 rounds, which will allow you to dispatch him without opposition.
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