I'll tell you what, back a number of years ago I was an inspired striper and letterer, I had all the best stuff, paint in many colors and all the different brushes and I started practicing. After a good amount of practice I found out that I didn't have it, not by a long shot. I couldn't put a stripe that was worth a darn and I have a LOT of respect for those who do.
To put that wheel in something, spin it, and using a Mack striping brush to lay a stripe around it? I can't imagine it looking very good at all unless it was done by a pro, you are asking an AWEFUL lot to pull that off. It's hard enough to lay a decent stripe along a straight edge. I am thinking the idea on painting the rim then masking off the stripe is the way to go if you ask me.
The "On Shot" paint is cheap, a Mack Dagger brush is cheap, give it a try. And if you can do it, super, and if you can do it, keep it up because you may just be one of those people with God given talent to stripe!