For wheel/tire combos, I've had pretty good luck with painting the wheel first, then chuckin' the assembly on my dremel tool, run it at low speed, and hold a brush full of tire color paint against it to paint the tire.
Normally, the only time this is problematic is when the wheel is very out of round.
Also use this to sand tires down to get rid of molding seams or if they are vinyl, to add some "wear" to the tread. Old slot car/model car trick from years back....(anybody remember the "Auto World" catalogs???...)
If you can mix your paint types, wheel color acrylic, tire color solvent based, (or vice-versa) cleaning up mistakes is pretty easy, as the cleaning agents don't harm the underlying color as easily.