In the end he has a perfectly serviceable boat for the area he sails in, it's sound and did not break the bank. If you go into these deals with your eyes wide open, and with a good surveyor you can do well.
Good point. The money and time he's put into it will never be recouped in dollars, but that's not the point. Old boats are just about the opposite of "fixer-uppers": you can rarely "flip" them and pocket a profit.
Having said that, if you find a boat with good "bones" (and this Bristol 29 sounds decent and is a notably good "couples/coastal/cruiser" boat), then you can put in the same amount as the purchase price to fix it up, but after that's done, the running costs are generally trivial. The amortization period is over 15 or 20 excellent summers, after which it seems like you got to enjoy the boat almost for free...