@Anstigmat:
I went thru the painting process two winters ago, including researching having someone else do it. Bottom line - Marine Painting Shops (Boatyards, and Marine Paint Specialists) are booked MONTHS in advance and unwilling to do such a small job and very expensive. I think I was getting priced around $3-4K when I just gave up. This is North Carolina, which is just as "boaty" as Maine, but more powerboat-oriented. If you absolutely dont want to do it yourself, check out auto-paint shops, a lot of them pride themselves in doing custom jobs (helmets, furniture, and the like) . I was starting negotiations with one shop when a buddy offered my his (unheated) barn and I took the plunge painting myself.
As for the painting process itself, it's 95% sanding, filling, smoothing, cleaning, masking (bring plenty of GOOD masking tape!) and 5% actual painting.. and then sand some more. I STRONGLY recommend you do the whole process inside, if only to keep the outdoor crap off your freshly sanded surfaces. See my progress here:
viewtopic.php?f=1&t=5853&start=30Our winters are nowhere near as bad as Maine, but I did a lot of work in freezing temps, and waited for over 50's weather before most of my painting. Two tricks of the trade - space heater and heat gun (both have their dangers as well, though! We can discuss when you get there).
I'm happy to answer any questions if/when you decide to paint the boat. Final advice before you start...
Decide how "anal" you want to be about your finish before your start. Are you going to race? Are you going to a boatshow? If the answer is "no" to either, then go for a "workboat" finish, in other words "If it looks good from 3 feet away, then I'm happy, don't get any closer." There's definitely a point of diminishing returns, somewhere around 600-grit sandpaper or fixing your umpteenth tiny paint run.
Get good paint. Assuming you are dry-sailing (trailer), you don't need specialized bottom paint, topsides paint is fine. Get yourself a nice enamel that self-levels (as much as possible). I'm in love with Kirby Marine Paints:
https://kirbypaint.com/collections/kirbys-marine-paints, but up to you. (Kirby is very responsive on the phone too). Petit, Interlux, etc are also great. Budget some $150-200 for the paint. Good paint = less work. I was able to "roll and tip" the Kirby's, was very happy with the finish. The other high-quality paints should be the same, you WANT to "roll and tip" (look it up, and yes, you can do it solo).
Anyway, painting the DS is relatively easy but you have to think through and plan each step. There's lot of little details and different ways of doing things.. how to fill gaps? Crazing/small cracks? how to sand without taking off the gelcoat? Best masking tape? Best roller cover? etc, etc. Much has been discussed already on this forum and there's advice (and videos!) all over the internet, so do your research. Don't be intimidated though, it REALLY is easy and you can erase (sand out) your mistakes. Besides, mistakes beget experience!
Best regards,
Tom