Well, most people don't wear armor, actually. Many Jedi and Sith forego armor entirely because they don't want their movements to be impeded and Jedi don't want to be seen as warriors. That being said, Sith don't really care, so there's that. XD No harm in having a bit more defense than not.
And yep, a sidearm is always good to have.
EDIT: Just don't forget to pay for the licenses as well to avoid later trouble.
I should have a small armoury on my ship, so you certainly won't go dry on stuffs like "pistols". :-3 "Pistols" should be to spare in various type for a variety of local gun laws. Armor for various kinds of terrain as well.
MN 10 + heavily modified. :-3 So yeah, won't be a star destroyer, but it's privately owned and get fly/land in atmosphere. Not something the "rebell scum" will want in their territory. They shouldn't worry however, either it will be a peaceful visit, or one that makes peace.. eternally. ;-3
Wha-? ...I mean... yeah, of course. Why could you not?
You can always ask around, have a look at the surveillance system, ask loyal agents to keep an ear out... heck, you could even have them fill up anonymous feedback forms if you want. Most officers don't give a damn, but if Wray does, there's nothing stopping him from building up loyalty however he wants as long as it's not against Imperial regulations or direct orders.
Nothing is impossible, it just hasn't been done yet.