As the current owner of a 26 foot boat that started out at $6500 and has now cost me almost $30,000 and is still on dry land, let me give you some cheap advice.
1) If you buy a fixer upper make damn sure you have some place to keep it for FREE. A marina is NOT the place!
2) If you think the work will only take a couple of months spend the money to have it hauled to some place FREE. If it takes a year you break even, if it takes 3 or 4 years the $2k for hauling each way will suddenly look like a bargain.
3) Little things like Honey Do's, Grandchildren, your job sending you out of town, Prostate Cancer, that kind of thing, some how eats up a lot of boat time.
4) The $10K boat was once a $100K boat. All the parts you will need are priced for the $100K boat.
5) Learn the difference between Used and Used Up. Many one owner boats are Used Up, while boats that have had several owners doing upgrades my only be used.
6) If you are really really handy, and can do fiberglass, carpentry, metal work, electrical, and mechanical, then you REALLY need to get a second opinion from someone else, preferably a surveyor. You'll think "I can fix that!" way too often.
7) Boats deteriorate continuously, even when you are working on them. It is easy for the deterioration to outpace you, it never quits, gets tired or frustrated.
Yesterday I went down to the boat, said F it, and went for a couple hours in the sailing dinghy on a local lake. Man's gotta sail you know?
Gary H. Lucas