ASA and PSIA Instructor
Join Date: Apr 2000
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need some help
Ok, that should get you into the game! So here''s my 10 cents...
Look for a popular model around 30'' in sail-away condition, preferably mid-''80s or newer. ''30 should provide minimum camping-style accomodations for a family. 30'' may sound big, but you will find the boat shrinks quickly after some use. You might have an experienced friend or a captain sail with you for the first few days until you past any intitial stage fright. Read everything you can and sail on other boats.
I don''t know what boats are popular in the area you mention, but Catalina, Pearson or O''Day would come to mind, and Cal at the higher end (Cal 28-2 is nice!). Given lake sailing you could consider newer Hunters, along as their resale market is solid. I would stay away from any fix-me-ups as the costs of engines, sails, or hull repairs are very capable of making even a free boat too expensive...
Focus on buying a popular model for a fair price, so you can sell-out later if plans change (or you want to up-size...). Always hire an experienced, qualified marine surveyor to complete a thorough survey done. Get some quotes, then hire the most expensive surveyor, provided he can explain why he/she is worth the cost and even then check several references...
Good luckm, and hopefully others will add to these comments.