You are not insane fools at all and having a tight budget will make it more of an accomplishment for you when you are doing it. If you have got the fortitude to do the cruising (including the Thorny Path) then you have the fortitude to learn what you need to know and to do the work needed on the boat. It can be done with your budget, with safety, but perhaps without a great deal of comfort. We met two big Norwegian guys (think Vikings) on an Albin Vega 27 in the eastern Caribbean. That would be something like 5000 miles from home. They were having a great time. Also met a fellow from California in the south Pacific on a Bristol 27 with no engine. He sailed the boat and had a sculling oar for moving around in an anchorage if there was no wind.
I would not look at the bigger is better type of boat. I would look for a boat that is tough and simple (and therefore cheaper to maintain). Yachtworld is a great resource but may not have the best prices since all boats are being sold through brokers and brokers are not going to be involved for really cheap boats. Look at eBay (local boats that you can see), Craigslist, local sailing mags/boat for sale mags. signs at marinas, etc for the real bargains. Ask local marinas if they have abandoned boats and what do they do with them. About four years ago, a marina we were visiting in eastern CT had an auction of boats that had been abandoned by their owners. A Dufour 30 which would meet your needs well went for $100. So be patient and do your homework and ask questions (as you are here).
Also, as several people have mentioned, you MUST do virtually all of your own work to make your goals feasible.
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!
Last edited by killarney_sailor; 12-14-2011 at 12:10 PM.