Join Date: Dec 2003
Location: Needham, MA
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I have a 1973 O'Day 27 that I bought as a project in 2007. The major problems were a fist-sized hole in the deck at the bow where the pulpit stanchion had been torn out and softness in the cabin sole. However it also had decent sails, a working engine (mine is the outboard model), hull spars and rigging in good to very good condition, and the interior was in very good shape. I paid $500 for the boat, $500 for the 12hp engine.
Do you have experience with fiberglass & epoxy? If not, sounds like you'll need to learn soon. I estimate it took me about 100 hours and $1000 to initially get it in sailing shape (granted that cosmetically it it still a work in progress, and I have made additional upgrades since then).
An O'Day 27 in good shape sells for between $4k and $10k. However, with all those problems you shouldn't be paying $1250, or perhaps anything. Get a survey done - even though the purchase price is low the time and money that a fixer upper needs can make it not worth it even for free. I did not have a survey done until after purchase but it produced no big surprises and I learned a lot about the boat. Overall I consider myself lucky with how things came out.
As far as the model, I have been very happy with her for the type of daysailing/weekend coastal cruising I do. I just returned from a singlehanded 3 day cruise to Cape Cod and Martha's Vineyard. If you have any questions about the 27's sailing abilities or other characteristics let me know.