"Pre-tirement" - planning

[Aaron_S]

I live in North Dakota, 53 years old and trying to look ahead for retirement.

I have a place on a lake for my summer weekends, but I don't enjoy ice fishing as much as I used to. I spent lots of time on the water have made 150+ mile weeks before.

I plan to spend a few weeks in Florida this February checking out boats, maybe going to a sailing school, talking to folks at marinas, hopping on board with someone who needs an extra hand - generally getting a validation of investing in the winter liveaboard lifestyle.

In subsequent years while I am still working, I would gradually spend more weeks during the winter in Florida and long-term consider a more full-time boating experience. My seasons would be May - September (Fishing), October - December (Hunting), Jan - May (???)

Here's my question - since initially for the first few years I won't have days or weeks to wait for a sailing weather window, but still want to do some exploring along the coast and keys, would it make sense to buy something smaller that I could use for a few weeks/ months and park (trailer) for the remainder of the year?

I have a medium sized dog that needs restroom breaks. (Leaving him home this year.)
I am comfortable with camping.
I am in good health. (non smoker)
While I am handy and mechanical, since I have limited time, I don't want a project.

Thanks for your feedback.
Aaron