Yeah I cant say we've seen a Vagabond rebuild. This will be interesting. Good move on dumping the OMC but you'll have transom work to do inside and out.
Gelcoat is big bucks from what I've heard. You might want to scale that back unless you have a fat wallet. Stress cracks aren't a huge deal. Unsightly, yes but as long as they are not structural, it can wait. There are folks around that can fix those too and if you're going to re-gel or paint, maybe you can do some body work yourself?