A Navy vet myself and looked at things pretty much the same way you are now. I found the boat and am in the middle of my final phase of refit. I do not live in the US and have not for some time, so I do have as good an idea as anyone regarding the where.
Your basic idea is sound. The Carib does offer a lot. I have lived and worked in the region for many years. A smaller boat offers some advantages, though it is an ongoing debate about what the "right" boat size would be.
I would love to keep up with your progress and offer any assistance if needed. Just let me know. It is a big change going from war ships to sailing ships. They do not dock the same way