If you store it outside, will it be in your yard where it is secured with a fence or something, or on the street? If it's somewhat secure get the bigger boat. You won't regret getting the better boat that's for sure.
I've never thought about this because my boat is always stored in my garage, but the guys that store their boats on the street sure have things difficult. The gear you need to remove and replace each time would put me off owning a boat. Especially if you have expensive gear like batteries, sounders, gps, minn kota etc.
I prefer a painted boat as unpainted kinda looks a bit unfinished to me. Just personal preference.
Fab your rig still looks like you picked it up yesterday. Well taken care of....