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post #2 of Old 09-29-2008
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Hi Kurt and welcome. It would be hard to go wrong with any of the small production boats in the 20-25 foot range for casual lake sailing and overnighting. Catalina and Hunter are two popular brands that still produce boats...and there's lots of others that are out of business but still popular in the used market. (Oday, Tanzer, Pearson, etc.).
You might start with your towing capacity and whether you want a fixed keel or centerboarder since trailering is a key part of your decision. If you are gonna single hand the boat, then raising the mast will be an issue and you may be better off in the 20-22 foot range.
I wouldn't worry about all lines being led to the cockpit as a condition. You are gonna have two halyards and all sheets will be in the cockpit on any boat. It is easy to make halyards led to the cockpit with a block or two and a rope clutch.
FWIW, I started off on a Catalina 22 and though it was no racer...we had lots of good use out of her and many weekends of fun and she was easy to trailer and raise the mast on with a gin pole.
Assuming a used boat...condition will be far more important than brand and price for your purposes.
I'm sure others will chime in with other suggestions.

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