First post BTW. Have a TJ Rubicon that I will be selling soon and have made final arrangements to buy a used JKUR that needs a little TLC.
On the wheel painting. Over the years I have painted my wheel many times. Best time to paint is with the tires off but that can make lots of extra work. It can be done with tires on but best to paint with old tires on just before getting new ones. That is what I will be doing soon.
Check out utube, lots of wheel painting videos.
I have found Rustoleum semi gloss works well. Process is clean wheels, lightly sand, if chipped you can use filler stuff, scuffs can be sanded out, if replacing old tires don't even need to use tape and paper.