Is now the time?
Moving aboard is a great idea. Given your real estate, you will have a foothold ashore if you change your mind. However, I would seriously suggest you reconsider your choice of boat and instead go for fibreglass construction. Beautifully maintained wooden boats are gorgeous (to look at) but will either break your pocketbook or your heart. In addition, a glass boat will have much more room inside compared to a wooden boat.
Sid in Florida