Funny you should mention a Catalina 22. I love those boats, fun, cheap, plentiful but would you take your 22 into the gulf? After reading some of your posts I wasn't sure if you were kidding or not.
Well I would, I guess I thought you were asking about a coastal cruiser.
I wanted a Catalina 25. I grew up sailing a Tartan 30 & 37 so a 25 was as small a I wanted to go.
I ended up with a Catalina 22. It fits in my driveway, and I end up actually sailing it. I'm not sure a bigger boat would work for me. (not that I don't want one!)
I think as a pilot, safety is 99% judgment & 1% equipment. People fly Cessna's around the world, it's not my idea of fun or smart, it has been done though. Knowing your limitations as in not putting yourself into a position that relies more on your boats strength vs. you ability to sail her.
So since you are getting back into things, a C-22 might be a good way to go. Certainly a Catalina 25 is a more capable boat than the 22 and I do not plan on leaving the waters of Biscayne Bay (unless I move)
Either way a 22 or 25 just be safe no matter which boat you choose!