Re: Old boat and fix it up or newer boat with few frills?
Only you and your wife can decide what's best for you, but....
Since you are going to be using this boat in retirement, some things to consider:
An older fix-it-up is going to take lots of work and money. First, of all, are you (and your wife) fix it up people....i.e....have you /are you a person with a record of accomplishing projects...building a deck, repainting a house, building a cabin or extra room, rebuilding a car or engine? If not, I would suggest that you might be better to get a boat that already has everything in more or less working order. On the other hand, if you have a record of large hands-on projects, an older boat requiring some work might be an enjoyable project. It is my belief that working on boats is somewhat more difficult because of the various curves and unlevel surfaces, so it could be a challenge. The end result of repairs (sometimes called upgrades) might be not so great for a newcomer.
If your dream is to fix up a boat and the sailing is a secondary, follow-on dream, a fixer up might work. But if the dream is to go sailing/cruising, and fixing up is only a means to get there, then go for a boat that you can use immediately without a lot of work.
Retirement years go fast....so do what you really enjoy. If you have to force yourself to do those fix up projects, the dream of going sailing might fade fast.