I have a funny feeling most of the boats in Haiti are hauling chunks of broken concrete now. The Question Steve asked about Cat 30 - Anything is fun to sail!! But if you buy a Catalina there are those on this forum who will give you a lot of static! Personally I have never owned a Catalina or a Hunter, but have spent a lot of time on both. My favorite is O'Day (I owned a 28 for many years) but now have a big heavy slug for comfort. I would probably have kept the O'Day 28 but the inside headroom was only 5-10 and my wife is 6-0 and I am 6-6. When we were in our 20's this was no problem, but 60 year old backs and necks cannot take the strain of constant crouching. To the question of affordability, I sold my 28 for 14K 6 years ago when the market was good, and she was in great shape. In today's market, you should be able to find an equal boat for 10-12. If you can find a satisfactory fresh water boat, you will avoid the spar and rigging corrosion problems inherent in salt water. My boat would have serious problems if it were in salt water. The 37 Endeavour has a keel stepped mast, which other threads on this forum say (rightfully so) will always leak. Salt water in the bilge will attack the aluminum fuel tank and aluminum water tank, both of which are in the bilge. I had a friend who had an Endeavour 42 who had fuel in his water supply and water in his fuel tank because of this.
First....I hope everybody has dug through their pockets to help out our friends in Haiti. I wanted to go down and help but am presently over committed to other very pressing problems.
I am darn close to 6'6" myself. Now in my 50's, comfort has become a large issue. So I would listen closely to any advice that you gave about boats that are kind to giants.
I have a good budget right now, I could spend over 50. I have been a cabinet maker and can do various maintenance on a good, older boat. I am looking for a boat that tends to hold its value for a couple years.
I want to cruise around N and S America for a couple years.