Thanks everyone for your input. Jay, I will be emailing you, thank you for being willing to be a resource. To answer some of your questions, the purpose is this...

I am retiring next year from teaching. I am only 53 (almost) years old so will be working something part time but my schedule will be flexible. My husband is 5 years younger and works for the forest service here in Colorado so he has some time to still put in before retirement. I was brought up in the Caribbean and have a longing to come "home" although I have lived in Colorado for 28 years. Our hope is that a job would open up for my husband in Puerto Rico or any of the USVIs (he could transfer over from forest to park service and still keep all his benefits) but that hasn't happened yet. My brother has a 444 that will be coming out of Sunsail charter in June/July. I have owner privileges on that boat but in order for both our families to do the sailing that we want to do (especially once I retire) I need my own boat. Plus it looks like he will most likely put that in private charter based out of St. Thomas so anytime I would want to use it he would be losing money. I want a Catamaran and can't afford to buy it out right at this time. Putting it in charter would allow our mortgage to be paid (guaranteed) for 5-6 years. Our hope is to be down there in 5-6 years as the boat comes out of charter and we would either move aboard or keep her for our personal use. At this point we would be able to comfortably afford her mortgage because we will be selling stuff here in Colorado. I also like the fact that with Sunsail/Moorings or Dream Yacht we can also sail in other places in the world. In fact we are excited to go with my brother to Tahiti in April.

That being said, I am willing to look at all options. We are going to the Miami Boat Show in April which we are looking forward to.