Had some time to get a few thoughts down.
A raccoonish kitsune seems like the best racial choice. From there, rogue, ninja, or investigator look pretty good in terms of getting the right/enough skills and the appropriate style of combat. At that point, I think it comes down to the skills I want to invest in and what features I want.
Stealthy acrobatics was a big part of Sly’s skill set, as was disable device, and disguise.
Any ideas on how to get his weapon emulated in Pathfinder? It’s basically a shepherds crook, but ideally I’d be able to finesse it.
I think the burglar, Heister or roof runner (last 2 especially) are perfect fits for sly. Hes all about moving in without being seen, and getting away if noticed.
Bentley is a ringleader bard for sure.
And The Murray is a vigilante/barbarian/rogue driver.
And I agree with AVR about the hanbo but... in all honesty if you want a crook... use the crook!
Damage 1d4 (small), 1d6 (medium); Critical x2; Range—; Type B; Special reach, trip
Category Two-Handed; Proficiency Exotic
Weapon Groups PolearmsDescriptionThis common herder’s tool is a wooden pole with a hooked end. When using a crook, you can ignore the penalty for not having two hands free when making a combat maneuver check to initiate a grapple against a creature you threaten.