I seem to be the only one with this problem since I cant find much info other than some corny looking CF stick-ons

Anyways the black vinyl surrounding the b pillar and around the rear small window on one side is starting to crack and peel. Of course underneath is the stock color which is AS. I want to have this painted either semi gloss or flat black but i want to know what is involved in doing this to avoid painting the rubber surrounding the black trim. Will the rear small window need to be removed to peel the rubber trim away?

Has anyone ever done this or have pics. I want a good job done not just spray can it,plus I am by no means a paint guy.

thanks