You guys hit everything I was thinking. I'm in my 50's, owned boats all my life. My gear head brother ended up as an engineer in the marine industry. So rigging and maintaining boats is easy and I actually enjoy it.
Oddly enough, my Bro said they use Carefree boat club now for some test boats.
I'm a center console guy, I went to Pro-Line boats 20 years ago. I have friends on Erie, Michigan and Superior with larger boats, so I have been able to avoid owning 26' and up stuff. In certain parts of the country I can also "borrow" some time on the R&D boats my brother uses. So I am familiar with a lot of boats and different waters. Only salt water I have done is Ocracoke Island, that is an interesting place for sure. Lake Erie is shallow and prone to turning to shit fast when the wind blows. I could see Tampa being like that.
I met a couple kayak fisherman on Double Branch river, and they gave me the feeling Tampa bay itself is a real shit show on weekends. That's expected.
We are in our early 50's, youngest daughter graduates college next month, we actually have the time to enjoy doing some stuff. We both enjoy fishing and being out on the water. We were getting ready to get a new boat last year, when she got recruited to Tampa. A good friend moved there, then he saw a great job for her.
The interesting thing is, he just joined a boat club yesterday, not sure which one yet. He doesn't fish, but his wife does. So life just handed us a great way to check it out further.