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I have a question or two about the Dirty Trick combat maneuver. For reference, here's the block from the PRD:
You can attempt to hinder a foe in melee as a standard action. This maneuver covers any sort of situational attack that imposes a penalty on a foe for a short period of time. Examples include kicking sand into an opponent's face to blind him for 1 round, pulling down an enemy's pants to halve his speed, or hitting a foe in a sensitive spot to make him sickened for a round. The GM is the arbiter of what can be accomplished with this maneuver, but it cannot be used to impose a permanent penalty, and the results can be undone if the target spends a move action. If you do not have the Improved Dirty Trick feat or a similar ability, attempting a dirty trick provokes an attack of opportunity from the target of your maneuver.
If your attack is successful, the target takes a penalty. The penalty is limited to one of the following conditions: blinded, dazzled, deafened, entangled, shaken, or sickened. This condition lasts for 1 round. For every 5 by which your attack exceeds your opponent's CMD, the penalty lasts 1 additional round. This penalty can usually be removed if the target spends a move action. If you possess the Greater Dirty Trick feat, the penalty lasts for 1d4 rounds, plus 1 round for every 5 by which your attack exceeds your opponent's CMD. In addition, removing the condition requires the target to spend a standard action.
1) Can I use my weapon to make the attempt, thereby gaining the benefit of enhancement bonuses or the Weapon Focus feat, as I would when using my masterwork flail to perform a Disarm? Or is it done independently of my weapon (as with Grapple)? Or does it depend on the individual Dirty Trick?
2) This is a little more of an advice question, but is Dirty Trick worth bothering with in Society play? I'd use it all day long in a home game, but its description makes it seem more fuzzy and "play it by ear"-ish than most, which makes me hesitant to consider it for organized play. Thoughts?
Thanks everyone!

Some call me Tim |

1) Can I use my weapon to make the attempt, thereby gaining the benefit of enhancement bonuses or the Weapon Focus feat, as I would when using my masterwork flail to perform a Disarm? Or is it done independently of my weapon (as with Grapple)? Or does it depend on the individual Dirty Trick?
Rules-as-written: No. Most of this maneuver is in the realm of GM fiat anyway. So, as GM I would look at what you are trying to do. Kicking sand? Nah, wouldn't help. Pantsing the enemy? Nope, flail would get in the way. Hitting a foe in the naughty bits. Heck yeah, a flail would help.
2) This is a little more of an advice question, but is Dirty Trick worth bothering with in Society play? I'd use it all day long in a home game, but its description makes it seem more fuzzy and "play it by ear"-ish than most, which makes me hesitant to...
I always recommend steering clear of any feat, skill, combo, that relies on a particular interpretation of the rules when in organized-play. The last thing you want to do is gimp your character because your new GM doesn't think poking your opponent in the eyes like the Three Stooges is funny.
In this case the rules are fairly clear that you get to apply a condition of your choice, so I think most judges wouldn't be a problem. The 'crunch' of the rules is straight forward even if the 'fluff' surrounding it might be vague. Also, I would not expect to get any feat or weapon bonuses to this roll.