I suggested open carry to my dad once(or was it in a gun store?), was told that they would consider the holster to be partially concealing the firearm, and therefore it's concealed.
If (big if) you get stopped and searched (for whatever legal reason) and a cop finds you in the possession of a bag containing a gun, pepper spray, flex cuffs and the like and he's probably gonna be less likely to think "warbag" than he is to think "rape kit", especially during winter if you've got a ski mask in there.
FWIW, I'm in the "I'm not LE, I haven't been trained to cuff, I don't carry cuffs" school. Gun? Check. Less than lethal? Check. Flashlight? Check. Cuffs? Nope.