Ahn.... the joy of painting

First, there's plenty of really smart folks on this board who will be very happy to help you. I'll throw in my $0.02, but read what others have to say and do some forum searches.
Second, fixing a badly-done paint job takes a lot longer than just doing it right.
BUT - painting is a winter project! There's nothing wrong with your boat from what I see in your pics. It can wait. Sand/strip the peeling paint off, just so you're not stepping in it while sailing, and then GO OUT AND SAIL! It's a plastic boat, nothing will get hurt by sailing with it as is, cracked gelcoat and all. (*See P.S. BELOW*)
Here's what I'd do... go over the boat with a paint scraper or spatula and get the worst of the peeling paint off. Then strip it with my favorite paint stripper - CitriStrip:
https://www.hardwareworld.com/p9w77kc/C ... n9EALw_wcBGreat stuff, let it sit for an hour or at most overnight then scrape off the gunk. Here's how I sailed my DS1 last season, stripped down to her "undies":

- Stripped!
- FallsSail.jpg (44.02 KiB) Viewed 1164995 times
Sailed perfectly fine, even if she looked like a freshly-peeled egg

.
When winter rolls around, get your boat under cover somewhere (preferably heated) and do a good job on her. I *LOVE* Kirby Paints:
https://kirbypaint.com/collections/kirbys-marine-paintsBut you can paint her with anything from Rustoleum (they make a marine paint!) to your-wallet-is-the-limit.
Good Luck and Fair Winds!
Tom
PS - OK, things that CAN get hurt - dry rot in any of the wood parts, a split in your rudder or centerboard that lets water get into the core, and take a look at the re-enforcement right behind the lip of your cuddy. If it's like most DS1's, theres a length of iron rebar glassed in to hold up the lip. Make sure that there's no cracks, etc that would allow water to infiltrate and rust out the rebar. I mention the rebar because that center post makes me suspicious... could be there to just make the hull stiffer (good thing!), or it could be there to "fix" the rebar. Double-check.
PPS - Wow! Who put a double floor on your boat? And that hatch forward of the centerboard? This isn't one of the "new" DS1's from Precision or CCD is it? And that lock-wheel on the centerboard lever! Cute, what happens when you hit a rock while the CB is locked?!? I'd rip-and-replace those wood coamings if I were you. Can wait till winter, but you show they are already rotting. Anyway, as long as she's not leaking and the mast is staying up, go sailing! Worry about it in winter.