Wifey B: Well, if you hook up with Gilligan, then all this other stuff will quickly become totally irrelevant as you'll be stuck on an island. The good part is food seems plentiful and you have Ginger and Mary Ann but sorry to tell you, I think they're faking any interest in guys and really getting it on with each other only.
Capt John and Janice were good suggestions.
When you read, you being with ABC, when you sing you begin with Do, Re, Mi.
Read that carefully, as there's a lot of wisdom to be learned from a simple song.
You need to slow down, back up, put yourself on pause and chill. Think of what you want your first boating experiences to be. You mentioned relatives in places you'd go. Think only of the boat needed for your first year or two of boating. Don't think more. You aren't there yet. You're going to overheat your brain and have it short out on you.
I got started with hubby on a lake in NC. We had a bowrider and we could go the length of the lake in less than an hour, but we'd spend days on the water, enjoying it, seeing every inch, all the other boats, just having fun. I never imagined what we're doing now. I did one time go on a Sea Ray down the TN River and loved it and thought that might be a nice place to retire. Never did I imagine the boats we have now, didn't imagine cruising in Alaska or down through the Panama Canal or in the Caribbean or Bahamas or up and around to Montreal or doing the Great Loop. It happens. It grows on you, but don't try to short cut or force it. Enjoy the beginning first. Focus on the early years. Then it won't matter how far it goes, you'll be enjoying it.
First thing I'd do if I was you, this summer I'd go find a way to get on the water. Go with friends or relatives or rent or charter a boat, even if just renting a pontoon. Get out there and start the process. Slowly, in the midst and nebulous cloud you're currently floating around in, some kind of picture will develop and it will be beautiful.