I've not had problems with paint sticking, but I also try and get all of my caulking done before I plastidip.
My typical procedure is this:
-fill any large gaps/cracks/imperfections with silicone caulking, smoothed in with my fingers
-At least 2 coats of PVA glue and water, mixed 10:1. I don't water it down much at all. I also keep an eye on the coats as they dry, usually coming back every half-hour for the first two hours to knock down any runs with a damp paintbrush. It's A LOT easier to wipe these down while still drying than to cut them down later.
-After PVA, I shoot a couple of coats of Plastidip, just enough to get a solid color base. The uniform color will make any knicks/gaps/etc. immediately pop out, so after the Plastidip dries I go through and finish filling imperfections with more silicone, and spray over the repairs with Plastidip.
-A final heavy coat of Plastidip to get the color all uniform, and then I go in with my primer/paint. I also try to handle the pieces as little as possible once they are Plastidipped, just to keep them clean and keep oils and such out of the finish.
As for using after painting....
I had to modify a suit a while ago
after it was painted and ready to go, building a new reactor insert and bezel in the chest to fit a custom piece. I cut out the old bezel, made a new one from foam, and then did all of my regular sealing work before gluing it onto the painted chest. The reactor bezel had a slight gap due to the curvature of the chest panel, so I then came though and filled the gap with this stuff:
Nothing fancy about it, I've gotten it at Menards and Home Depot for a buck and a half.... Anyways, I applied it, smoothed it with my finger and a wet rag, and let it cure. The next day, came through with my Rustoleum 2X primer/paint and painted the bezel and chest surround to cover the repair. Looooong story short, the results looked great and I never had and problems with adhesion or finish:
Will this always work? Of course not. I try and spray any late repairs with an extra coat of Plastidip before priming and painting just to give an extra level of protection. I have never had any problems, other's mileage may of course vary. :rolleyes