We had similar requirements as you. Bought a Cataline 27 Tall Rig. Absolutely love it.
This past year, we spent two months on board in the Bahamas. It handled the Gulf Stream crossing and island hopping quite well.
It's a bit small for living on (ha!!!), but it does work. A great compromise between size (it's still trailerable - we trailered it from Montana to Florida) and yet is liveable too.
The heavy fin keel handles weather fine.
A very very popular boat so replacement parts are super easy to find - even though the boat is 40 years old. Get to know the people at Catalina Direct:
. They've got everything (I mean EVERYTHING) you might need to replace on board.