Basic Painting Questions

I'm totally new to painting anything not to mention a boat. I have a rough-condition daysailer paintjob and I want to fix it, but I don't need it to be perfect, I don't need to be using the exact perfect paints for every part. In fact, I only really need to paint the deck/cockpit, since under the waterline is great and the topside is in pretty darn good condition.
My basic goals:
-Keep sailing as much as I can before fall
-Not have the boat get messed up before its time
What I don't need:
-A boat in "perfect, like-new condition"
-To use all the industry-standard methods on all the different needs/problems
At first I was going to totally strip the deck and cockpit, but then I figured why do the extra work if I could just sand it smooth and then prime/paint over the old stuff. But I realized even that is quite the job, as there are many attachments and sanding takes quite a while. Plus there's things that seem like they straight-up need fixing before I paint over them, like the bench backs which have some kind of old wood caulking that's coming out of them, and some cracks that go deeper than the paint (is that called "gel coat?" or is it simply fiberglass fractures? - pics included of all this below.)
So my basic thought is this: all I really need to do is sand/scrap the peeling spots this season, so long as the boat won't rot before I get to paint it this winter. Is there any danger in just sailing it as is, or can I just do a quick job with something like clearcoat after a quick scrape/sand to sort of freeze it in the condition it's now in? I know that if I start taking things apart to do a really good job I'll get hung up and won't be sailing until next spring (I'm not an efficient handyman.)
Pictures on google drive: https://drive.google.com/open?id=1nz-cN ... AK49_1P8p-
My basic goals:
-Keep sailing as much as I can before fall
-Not have the boat get messed up before its time
What I don't need:
-A boat in "perfect, like-new condition"
-To use all the industry-standard methods on all the different needs/problems
At first I was going to totally strip the deck and cockpit, but then I figured why do the extra work if I could just sand it smooth and then prime/paint over the old stuff. But I realized even that is quite the job, as there are many attachments and sanding takes quite a while. Plus there's things that seem like they straight-up need fixing before I paint over them, like the bench backs which have some kind of old wood caulking that's coming out of them, and some cracks that go deeper than the paint (is that called "gel coat?" or is it simply fiberglass fractures? - pics included of all this below.)
So my basic thought is this: all I really need to do is sand/scrap the peeling spots this season, so long as the boat won't rot before I get to paint it this winter. Is there any danger in just sailing it as is, or can I just do a quick job with something like clearcoat after a quick scrape/sand to sort of freeze it in the condition it's now in? I know that if I start taking things apart to do a really good job I'll get hung up and won't be sailing until next spring (I'm not an efficient handyman.)
Pictures on google drive: https://drive.google.com/open?id=1nz-cN ... AK49_1P8p-