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Here''s my 2 cents:
1) Learning on a smaller boat is good in my opinion. The larger boats are more forgiving than smaller boats, so I think you''ll be a better sailor if you learn on a smaller boat.
2) There is one boat that is definately in your size range, price range and has 6''5" head room(through-out the cabin): Morgan OI33. I recently owned one. It has a full keel. It weighs 14,500 pounds. It is definately a cruising sailboat. I sold mine since I was only really daysailing with my family on Lake Michigan and I decided to get a 26'' sailboat with a very small cabin and a large cockpit. What really sold me on the Morgan OI (Out Island) was the headroom and spacious interior. It has an almost 12'' beam. I am also 6''4" and I really did have headroom throughout. I could actually stretch out when standing. Most of these boats are in Florida, but occasionally you can find them in the NE. You can get one of these boats for between $20 and 30K. Definately have it surveyed to make sure it doesnt have any problems if you find one.
There will be some people that are going to respond that they don''t like the Out Islands for various reasons, but talk to people that own them and you get a different story. If you want any more info on these boats feel free to email me at: [email protected] and I can set you up with all the pertinent web sites etc. Good Luck Rob ~~~~_/)~~~~
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