GG, you are a lucky man! It may be that you and that boat were meant to be together with all of the events and circumstance that took place.

Halyard wrap can be taken care of as CPete pointed out.

I have not heard of a 4-stroke suffocating in one of our closed lazzarettes as they tend to be leaky yet not leaky enough for a 2-stroke.

Single speed winches are not that difficult to work on. BUT the springs and retainers can fly far and fast so disassemble them in a small, clean, well lit room the first go around. Someone once suggested a deep, roomy box helps contain things as well for the disassembly, you can more comfortably work on a bench until you get ready to 'respring' and reassemble, then practice the containment proceedure again.

Pete is right about the sanding. Watch out! My project started with a little punky wood at the base of the mainbulkhead. Of course if things get out of hand, do like I did and blame it all on Tim Lackey. When he chronicled the restoration of Triton 381 he made it look so easy that everyone thought they should do it.

Never tried bottom paint but Tim sure makes it look easy

It seems sewing is one of those skills that once you learn the 'secret code' it becomes much, much easier. But to learn the code you have to sew a few pieces and tear up a few seams.

I don't think there is anything on your list that can't be managed just fine. The golden rule is double the amount of time and money you think any job will consume and then you wont feel so bad about having to spend a little more than said amount!

Welcome aboard!