Looking at your picture, not withstanding the order of painting, aside from the badly worn section smooth gelcoat behind the winches, how is the rest of the smooth gelcoat of the cabin top and deck? I ask because painting a cabin-top is not a trivial quick process. If you can get away with not doing it, maybe that is the happier option. If the rest of the gelcoat is still serviceable with a cleaning and wax job, consider taking that route and just paint the area around the winches. With some thought, you can mask in a appealing geometric form in which to paint with a reasonably matching color.
I recently painted my cabin top with Perfection (second time - first done six years before). I like working on my boat, but this was a project I was not looking forward too. Which bore out. The outcome is fine. But I had absolutely no fun doing it and not everything worked out as expected = more days than budgeted. All hardware and handrails need to be removed, re-routing or removing running rigging to get it out of the way, sanding, removing old embedded wax with solvents, masking around ports, toe rails and everything, putting dots of tape over all open holes to prevent paint running out when painting, painting and sanding between coats and painting some more within the manufacturer's repaint window, removing tape (which by now has been on a while so often tears when pulling instead of just pulling up in one nice motion), reinstalling and re-bedding hardware, re-running all your lines, and clean-up and more. While each step may not seem like much, it all adds up to many hours and days.
In comparison, the non-skid section of my Cherubini Hunter (you've got one too!) has virtually no hardware mounted on it. Hence the process only clean, mask, paint. Done.
