Have been following your progress on the forum for a while and sure looks like you are proceeding carefully and logically with prepping your boat to cruise
I have only been on one S2 but it looked like a well built, solid boat and they do have a good reputation. Don't see any reason why it can't take you where you want to go. Other than limited storage
space the only real issue I see with a smaller boat is the relative motion. I've crossed the Caribbean
on a 32' boat and a 65' boat. On a day where I had to hold on to move around on the 32 I could stroll the decks on the 65.
As long as you aren't distressed by the motion then no problem. It can be difficult to rest when the smaller boat is bouncing around so you need to plan for that on a long passage
. Island cruising even that isn't a problem.
Keep on keeping on. I'm not far up the road from you so if you're in the neighborhood and want to chat drop me a line. You can come by and look at a bigger boat that is mostly disassembled.