For starters, let me say I'm not totally against useing paint finishes on a boat. I did the blue band around mine to repair some dock rash from the PO when I first got it. I really don't have any first hand experiance with clearing over gel but it doesn't sound like a good idea to me either. Auto clearcoats are designed to be put over their coresponding basecoat not raw polyester so I would imagine adhesion to be a problem. You say you have been waxing the crap out of it so another problem is going to be getting all of the wax & silicone off. Gelcoat (especially aged) is rather porous and sucks that stuff up. I washed mine down with prep cleaner 4 times and still got some fisheyes.
My boat is an 86 also but has had a full mooring cover from day 1. The gel on the deck still looks like new. Maybe consider getting a cover for it and see if your wax job holds up better? Probably get one made up for about the same as what the materials would cost to do a respray.
If you really want to paint it, I would start by sanding thouroughly with 400 ,clean it with prepsol till your face turns blue. Then lay down a coat of epoxy primer in a color close to that of the gel. PPG sells it in different colors and it can be tinted. Then do the basecoat / clearcoat. That's the way you do a Corvette but then no one is walking on them either! lol