YES you can paint over the plastidip and it WILL hold up. I did this to the wheels on my last car and it worked out perfect. It only flaked when I PURPOSELY peeled off the plastidip because it stretches and the paint does not. Go for it!

 

Artwork over removable paint.... Of course it can be done, if you know what you are doing! I done this a few years back. Still going strong!

 

You didn't say what you were actually painting. If it's your wheels, save yourself the hassle and just lose the plastidip. I had the bright idea to plastidip my beadlock rings a couple of years back I figured I could just respray them if any of it got knocked off. Of course I knocked plenty of it off, but it there were always pieces sticking up so respraying it with plastidip would have just made it look worse. I just mounted new tires onto my beadlocks and decided I was just going to paint them this time around. The plastidip was a PITA to get off. If I would've stuck to the peeling process, it would have taken me over a week to do. I grabbed a wire brush attachment and hooked it up to my angle grinder and made quick work of it. I painted them black with a wheel armor black paint that I picked up from O'reilly's this time around. If they get scratched or marred, I can simply respray.

Plastidip

Wheel armor paint