There are alot of boats that fit the criteria you've laid out... and a lot will be up to your personal preference.
The criteria as I read it are:
Trailerable pocket cruiser capable of housing two people for short cruises, say up to a week, and daysailing, on the Great Lakes and other large inland lakes.
Compac, Catalina, Hunter, West Wight Potter, S2 and several others all make boats that would be suitable for those criteria. Your budget will determine a lot of what you can choose from. What kind of vehicle do you have as a tow vehicle, since the tow vehicle will also have a lot to do with what size boat you can get.
I'd also highly recommend that you reserve about $4000-5000 of your budget for refitting, repairing, modifying and upgrading any boat you look at. This is because boats, unlike cars, often need a fair bit of customizing to be best suited for the individuals sailing them. Some will want things like autopilots and lines led aft, to make the boat more suitable for single-handing, others will want refrigeration and cabin electronics, to make the boat more comfortable when at anchor, etc.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.
Last edited by sailingdog; 04-04-2008 at 04:22 PM.