Re: Old boat and fix it up or newer boat with few frills?
I think you have received some very good advice here that should give you food for thought. A few more things to consider.
- going to the Caribbean and doing a RTW are do entirely different things. The boat that would do the latter will do the former, the opposite not so much. A newer $100k RTW-capable boat will not be very big - at least partly since not many boats with this capability were built post 2000 and most that were built are much bigger and much more than $100K. I guess what I am saying in reality is that you may not much choice if you want a boat big enough to be comfortable around the world.
- you MUST be able to fix your own boat if you want to do extended cruising. It is not just a matter of cost. I am typing this sitting at anchor in Alor, Indonesia listening to the prayer chants from the mosques after a terrific touring the island - just the sort of experience that one cruisers for. If i needed to get work I could find a diesel mechanic since there are lots of diesel engines here (no parts for the Westerbeke but these guys are very handy) and that is it. Anything else needs repair you would need to go to either Darwin, Australia or Singapore and each is several days away (at best). It does not matter much if your boat is old or new, you still need to fix stuff. A friend here has an Oyster 54 ($2 million) that he bought new about 7 years ago. He is always fixing stuff as I am with my 30 year old Bristol (not $2 million)
- for your older boat range you mentioned 37 to 45 feet I think. This a hugely different range of boats. Imagine taking the 37 and cutting it in the middle and adding a room that is 8' by 13' and you will get some idea of the difference. You might want to think about displacement as much as LOA
-involve your wife completely in the decision at all steps. Visit both newer and older boats and see what she thinks. If she is happy your chances for happiness go way up. My wife was the one who decided that we should circumnav and she chose the boat from a short-list I had created.
Heading back to Lake Ontario for this summer. Relatively few stops along the way from Grenada. Martinique, Guadeloupe, St. Martin (must have something to do with the French food), then Bermuda, New England and up the Hudson/Erie Canal. We were going to go via Newfoundland and Labrador but June remembered that one of the kids is getting married this summer - details, details!