No need to use loctite with a nylock nut. If you remove the nylock then replace it with a new one. I would use nylocks where you can. Loctite is more for blind holes.
When you are looking for tins what do you type in the search box on craigslist? Or outboards? I get a little tired of looking through a bunch of boats I'm not interested in and hope I'm not missing some that I want to look at. So what's worked best for you?
You can buy paint at hardware stores with it already in the paint, but only a few colors. You can also buy a small bag of the the sand like nonskid material and mix it in the paint you want to use.
You will probably need to put the guides on the the widest point of the boat. If you put them at the back and the transom is thinner the the middle then it will be more difficult. I would put them at the widest point. Pics would help.