I own a '73 O'Day Mariner. There are likely problems that need to be addressed. If you are at all handy with a stirring stick, a paint brush, a putty knife, sand paper, wrenches, drill and maybe even a hand saw, there is very little that can't be made new again.
I bought my boat from a photograph, a phone call and the knowledge that I can fix anything with a little time and fiberglass.
It was stupid and I wouldn't recommend it, but it worked out for me. Mostly it was the phone conversation, getting to know the seller, that did it for me. That and the Mariner is a beautiful little boat.
Buying tips: look at who you are buying from. If their car is older but still in great shape, the boat is clean and any damage over the years has been repaired well, they talk like they loved their boat, know what they are talking about, and care about their world, they probably took good care of their boat until they decided to sell.
If there is grass growing on the bottom, forget it.
If the lines are rotting, forget it.
If the repair job in the bilge where the centerboard trunk started to crack at the junction with the hull is sloppy and inadequate, they ignored other issues or didn't do a good job with them either.
Does the deck flex when you walk on it?
If the bilge is clean and dry it might have a leak. If the bilge has water in it, it does have a leak, if the bulge is a little dirty but dry, you're good. If its too dirty, the owner is a slob or neglectful.
My Mariner has an iron CB. They rust and swell in the trunk sometimes. This can be fixed, but it is an issue. Mine wasn't bad at all.
If you tap the hull with a plastic hammer or screw driver handle you can hear where the core is rotting.
The Mariner sometimes leaks at the hull to deck seem. Water in the bilge when on the hard will help indicate that.
Beyond all the issues mentioned above, a thorough visual inspection and inventory are called for. Test the winches, they are expensive to replace. Work all the working parts like the kickup rudder. Drop and raise the centerboard. Hoist the sails and listen to them. Is the stitching brittle and cracking when handled? My replacement main was just over $500 and that was cheap.
Rust is another enemy. All fitting and bolts, turnbuckles and cables should be marine stainless or the appropriate material to prevent rust. Then there is the trailer. That can often make or break a deal. It isn't unusual for these older boats to not be in great shape, but the trailer is worth more than the asking price. They are expensive and hard to find used, so make sure that is in great shape too. You can save yourself a lot of expense, over the years, having a good trailer. Marina charges, storage, etc., life is easier with a good trailer.
Take her out for a sail with the owner and watch how he handles the boat as well as how the boat handles.
The age of your prospective boat can indicate problems, but it is not a problem in itself. There are still 100+ year old boats sailing out there, they have the advantage of being well loved and cared for by their owners.
I hope this is one of those boats for you. Good luck.
- Will (Dragonfly)