Re: Lack of Confidence
That is a good list. Personally, I'd fix the cockpit drains first since that can be a 'boat sinks' kind of problem.
The electrical is really a can of worms and can be difficult to really fix, and certainly to do properly. Corrosion and iffy connections can really make things hard to track down. Lots of time with a voltmeter and ohmmeter. A knowledgeable DIYer can do it certainly, but if you aren't confident that is one that might be worth paying someone to look at.
The diesel and trans service you can probably do yourself.
Excellent advice. Safety issues need to be tackled first. Next I'd look at the prop or some other small, isolated job which can give you a feeling of achievement when you cross it off your list.
Electrical gremlins can be awfully hard to track down, and it will do your confidence no good to go chasing after them and still be stuck 20 hours later. So take up the electrical system only when you're feeling a bit better about the whole project.
The only dumb question is the one that you didn't ask because you thought it would make you look dumb.