Paint v gelcoat
awlcraft. not awlgrip.
a boat of that vintage is not going to come back as good as a great paint/application.
Unless you paid a price for a boat that has been maintained , you will spend so many hours prepping and polishing to get that new shiny on top dull finish that 60 to 80 hours of painting will seem like a small investment.
furthermore. the condition of the deck is important. most 25 to 30 yr old boats have checks, nicks gouges, hairline crazing not to mention the molded nonskid areas and other elements that must be rapaired prior to refinishing or repainting.
Most of those beautiful paint jobs you see in the trade literature were done inside with building to protect the paint. and are going to be more difficult to obtain in a yard.
But if you can protect the boat during painting. The color depth and richness are unequaled.
I am not selling paint, But I have spent my fair share of hours on a dozen boats bringing back that gelcoat finish. I have had my share of successes, I have a 21 year old ski boat with like new colors, but she is not red, lives under a cover and costco shelter, and only gets two weeks of use a year.
Everything else.......Is a lot of work to keep shiny all year. the major advantage of maintaining your gelcoat is the ability to use a fairly aggressive jet wash down. You give that up when you put paint on. Out here in the pacific northwest, keeping the surface shiny is harder than it should be. maybe its the mildew on every horizontal surface, maybe its the dull rain clouds everpresent, but it sure seems like that finish should shine more. Like you, we only have about 5 months of the year warm enough to apply paint outdoors.
Maine sails advice is excellent, and shows the amount of effort required to restore a finish.
I have used variations of that method for boats on trailers, in yards and in the water. None of them are particularly easy on a large boat. Applying the proper cutting, polishing, and buffing pressure on the top of a ladder is er....is interesting. most marines do not care for abrasive refinisihing performed in slip. Tho lying on the dock with the boat sprung tight agasinst the dock is not too unconfomfortable of a position.
Since you are in Maine, the UV is normally less of an issue than the other weathering. But that size boat can easily exceed 40 hours for an new owner.
you could put 50 hours or so into restoring and polishing the gelcoat, and not be satisfied. Start with just the transom, If you are happy with it and get the finsih you want go for it. If I couldnt get the transom to the condition I want, I would be looking at painting, or shoot gelcoat again. but shooting gelcoat is an entire boat option only, just like paint.