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Does having a weapon in both hands create a penalty to attack just for holding two, or is it only when you want to attack with both on your turn? If a Gunslinger has a pistol in one hand a cutlas in the other would they incur the penalty even if they just attack with the cutlas in melee, or if at range they fire the pistol, would they have the penalty for dual wielding?

I think if they are attacking with the weapon in the off hand then they apply the penalty... at least that is how my group played it.

It's open to interpretation inasmuch as it is not explicit.

If you wield a second weapon in your off hand, you can get one extra attack per round with that weapon. You suffer a -6 penalty with your regular attack or attacks with your primary hand and a -10 penalty to the attack with your offhand when you fight this way.

Core Rulebook p 202

I think the key phrase is "this way" and that it refers to getting an extra attack per round rather than merely wielding (i.e., holding) a second weapon.

Looks like you are trying to save from sheathing/holstering/drawing/changing hands with your gunslinger. As far as I know, Pathfinder does not track handedness except for purposes of two-weapon attacks and shield bashes. Since what you're proposing isn't either, I don't see that there should be a penalty for shooting/swinging with your offhand. Also, who's to say your gunslinger doesn't always shoot with his left hand and swing with his right?

 Manchu wrote:
Looks like you are trying to save from sheathing/holstering/drawing/changing hands with your gunslinger.

I'm also trying to find out if I need to take Two Weapon Fighting at some point, or if I have a free slot. Quick Draw and Gunslinger's Initiative allow me to ready the pistol when Initiative is rolled, but there is not easy way to holster the pistol quickly that I have found yet.

We had a gunslinger who just dropped his guns when they were empty/when he wanted to do something else rather than holstering them, then he would have to pick them up after the battle (hoping that he could find them or that the combat had not moved on to somewhere he could not get back from ).

In this setting guns are rare and difficult to replace, not to mention apt to be stolen, so barring extraordinary circumstances casually tossing them around like that is not likely.

I bought a weapon chain for my pistol, would use my pistol as long as I could, drop the pistol as a free action, draw my sword as a move, and use my standard to attack.

Aren't there holsters which allow you to draw and holster as a free action as well (or at least minimise the amount of action required to draw/holster)?

I found the Endless Bandolier Wondrous Item, but it only allows retrieval "as easily as if from an ordinary ammunition pouch or holster", but says nothing about holstering quickly. There is another Bandolier that will teleport ammo into the pistol, but again doesn't have any benefit to holstering.

Didn't find weapon chains on the SRD.