Nice! The tubes look serviceable to me but I'd definitely get a pro to do the gash repair. Does Wing up north do Hypalon repair? My seams and edges look worse but then my tubes are 27 years old but still hold air after a couple dozen holes patched and a little internal sealant.
As they say on the boat building forum i frequent, "how do you eat an elephant? One bite at at time". Look over the boat and start making your list. It's one foot in front of the other. Don't freak out about how much needs to be done
There's a lot to do but none of it's rocket science. It's planning, patience, and time. All the info you'll ever need is available here and elsewhere on the internet.
Trailers aren't too hard either. Put your's up on craigslist and see what you can get for it. Big trailers are rare and somebody might need it more than you. A nice new trailer is going to cost a fair amount but maybe you can recover some of that. You can always make yours smaller and just scrap that axle.
Heck, want to trade? mine's a little short for an OB but plenty big for a IO.
Lot's of options. breathe....I went through all the same things.