Yes it is possible for a competent painter, but you'll likely need some minor body work as well. When I removed the white vinyl top from my 75 Duster I found rust was already forming underneath it, especially around the edges. And that was when the car was only six years old. Unless the car is garage kept those vinyl tops can cause serious problems. If your vinyl extends down the A pillars you’ll find that the joint between the cowl panel and the A pillar was never properly filled in at the factory, so that will need to be finished. As for holes, most of my trim was attached to raised metal pins that were likely spot welded in place. They were easily removed. If I recall correctly the two bits of trim at the bottom of the A pillars were screwed down, but that was it on mine. Once the vinyl was removed the gutter trim reattached with no problems.
