It's actually a lot easier to get the rings off and paint them, than to mask.
I've done both (resprayed them when I did my joey mod). And it looks a lot cleaner the second time around.
It took me a while to figure out how to remove the headlights, but once you get that down, it's a much quicker process.
Have you figured out what you're doing with the door handles?
Mine are still chrome Thinking about getting some high quality vinyl and doing it myself.