What was the driving thought behind you and your wife considering retiring on a sailboat? Did you see a book, magazine, marina, boat sailing while driving across a bridge? Did you read something about the cost and it looked cheaper than a house? Did you see a youtube and see how much fun it can be? Did you grow up thinking about sailing?
I don't ask it to be rude, but the answer to this question will also help. There's a lot of great reasons to start considering retiring on a sailboat, but then again, there are a lot of not so great reasons.
We're not retired and it's doubtful we'll live on a boat when we retire, but we like sailing. We got started because as a kid I always thought sailing looked like a nice relaxing day on the lake (like in the movie
Jaws). When the kids
left, I started watching youtubes and took many of the ASA
courses. We realize we like it but don't love it. We love the part-time chartering a "big" boat in the BVIs and we like sailing our small 17' footer around.
I got a lot of pointers from this forum and found the reason behind wanting to consider it helps the folks who a lot more than I how they can best advise and help.