Ron,
You are sick, sick, sick. You really should talk to someone about that "Fuzzy Fir" thing.
I've done so many roadwheels, I can't even begin to count them all.
And yes, I do paint both sides.
If I didn't, I would wake up screaming in the middle of the night that I didn't paint both sides!
What I have found that works well for me is to thin the paint a little (dip your brush into whatever thinner is applicable for the paint before you dip you brush in your paint). That way the paint flows better and will follow the crevase between the rubber and the metal on the roadwheel. This makes a nice definition line between the two without the headache.