Sarah, we are from Vail, Colorado and are also looking into having a boat in the Caribbean. I grew up in Grenada on a sailboat and will retire from teaching this year so want to get back as often as possible. My husband is actually currently looking for jobs on any of the USVI's and Puerto Rico either with the Forest Service (PR) or Park Service. (He can't retire yet so would want to continue in his career path due to benefits.) My brother currently has a boat in charter with Sunsail that we get to sail on about once a year but we want more time down there. Would love to hear what you find out.