First, welcome to the Hobie forum. The people here are very friendly and the advice is always sound. Like you I've sailed both cats and small sailboats including Sunfish, Lido's, Capri's, Cape Dory's and a few others. Since I moved to the Texas Gulf Coast in 2009 I spent almost a year just looking at the waters in the Corpus Christi area and trying to figure out what was going to serve me the best. I finally purchased a Hobie Oasis in 2010 and have never been sorry since. As a tandem, I can use it with another person or solo with no real hassle or problems either way. I also purchased the Hobie sail kit which is easier to set up than even a Sunfish. In your case however you may want something that can handle even bigger water. I think the Adventure Island may be a great way to go. You can purchase the extra tramps to go on the aka's for use when somebody else goes out with you. On the solo occasions the boat is already set to go with no further issues. Another advantage to the AI is it's capacity as a very good kayak by itself. This might be a huge advantage over a Bravo to you if you ever wanted to adventure into the Everglades. It's just a very practical multipurpose boat that is also quite fast and exciting. Good luck with your quest!