Sneak attack with Improvised Weapon Hijinks

[lemeres]

Pathfinder SRD wrote:

Catch Off-Guard (Combat)

Foes are surprised by your skilled use of unorthodox and improvised weapons.

Benefit: You do not suffer any penalties for using an improvised melee weapon. Unarmed opponents are flat-footed against any attacks you make with an improvised melee weapon.

With this in mind, I was curious how one would go about exploiting the bit about flat-footed condition. While Rogues may attack when their opponents are unprepared, you can hardly rely on that consistently. So the first idea to come up would be the disarm maneuver. This quickly brings to mind the whip, since it can be weapon finessed, allowing them to use dex instead of strength for disarm (at a distance too). A vase to the face to add injury to the insult.

Just looking at this for fun rather than a serious build. Any other ideas?

[Seranov]

Couple levels of Monk of the Empty Hand (maybe combined with Maneuver Master, if they stack) and then the rest of the levels as a Rogue?

[DM_aka_Dudemeister]

Interesting side-question:

Is a monster with only natural attacks considered unarmed for the purposes of this feat?

Can I slap a dragon with a fish and get sneak attack in?

[Seranov]

Sounds nice, but I doubt it. IIRC, you count as being armed at all times when you have natural weapons. I can't recall if that was something from the rulebook though, so grain of salt, etc.

[lemeres]

While I doubt it would be by RAW, and I certainly would not view it as such with the dragon in that situation, I could imagine circumstances where I would see a creature as honestly surprised. Monks and creatures with improved unarmed strike are considered armed, but that quality implies that they are trained in unusual combat or the general workings of a bar room brawl. But a random Lizardfolk knocking you into a chair, and then you use that chair to smash his face in? Yeah, I can see that working for a sneak attack.

Obviously this build is meant for more urban campaigns, so most of your opponents would be human or humanlike in reaction to you using random objects to try to kill them.

[blackbloodtroll]

This feat is useless against creatures with Natural Attacks.

[lemeres]

By RAW yes, but not all natural attacks are the same, flavor wise. Would a worshipper of Lamasthu with the Mother's teeth trait really be better able to react to a wine bottle smashed over his head with that 1d2 secondary bite than any other random person?

[blackbloodtroll]

Fighting RAW with Flavor, for pure mechanical purposes is frowned upon.

[lemeres]

Of course, I would never really plan to fight like this in a real game. I am just discussing the difference in the rules, which have to set simple strict guidelines to run a proper game, and the many intricate details of reality.

This very build is based on such a weird mechanic. How long can you attack someone with a mop and it still surprise them? By this feat RAW...forever. But eventually you would adapt and it would be like a regular fight. I'll admit though, I am probably weaseling like any proper player on this board. I apologize.