"Pipe Dreams" or is it really possible???

Dukesfin,
My husband and I have done exactly what you are wanting to do. 10 years ago we visited the island on a cruise and were actually looking into moving to Islamorada Florida in the Keys. The housing there was so expensive we were beginning to think our dream of living on an island wasn't going to happen. While in STT I happened to pick up a housing magazine just for kicks thinking it wouldn't even be possible. Well I was totally shocked. The rental prices alone were much cheaper than the Keys.
So we traveled by cruise ship 8 move times visiting just about every island in the Caribbean. Trying to make sure which island was right for us. While there were a few other islands we fell in love with they did not offer the security of being owned by the US that we were comfortable with.
So three years ago we took our first PMV trip. Hooked up with a great Realtor named Rosie Nichols and she started showing us property we thought we could afford. The first trip we were mainly focused on condos and let one slip away. We were heart broken but kept on looking.
The following year we came across a great duplex and last March purchased it. We presently have both sides rented and will be making the big move in November.
This weekend we are heading down for our final PMV. This will be the fourth and final PMV.
We have done all the homework this board has told us to do and it has made our dream of living on the island a lot smoother. They only things we have left to do this visit is to do some window shopping of all the items we think we will need to replace after selling everything here ( we are planning on give a few storage bins to relatives to keep) ( one full of winter clothes that we hope we never need again but just in case we need to fly back in the winter for a funeral or wedding, as that would be the only reasons to fly back in the winter, keeping in mind to keep the nicest of the winter clothes and getting rid of the other crap) ( the other we are filing with our Harley clothes, chaps, leather jackets and all those harely shirts that have long sleeves, and storing at our son's home in NC with the Harley so that when we fly back in the summer to visit we have transportation to go where ever and also drive up here to IN to see friends)
All the furniture is going alone with the house and only the most precious of items will be shipped ie...pictures, crystal, china,,,,going to finally start using all that stuff on a daily basis...life is to short not too...lol
As far as jobs go from our experience until you have a place to live they will not give you too much thought. Thus is why we bought the house first...and also for investment purposes. This visit we plan on doing a little job searching but mostly getting to know the people where we are interested in working.
We are both 48, have two married sons who are serving in the US Army so they aren't around here anymore. We do have two grandchildren that we set up savings accounts for so that anytime we need a grandparent or parent fix we have the funds to fly them to STT.
My husband is a bricklayer by trade but hopes to figure out what he wants to do when he grows up once we get there...pro bally something in the tile trade or possibly fishing or landscaping.
I have retired from a long career in the athletic business and presently went back to serving and am enjoying it so much that that is what my dream job is....serving at some great place by the water and getting to see it everyday.
If you have any questions feel free to email me directly as I don't get on the board as often as I use to.
im4whs@aol.com
Good luck and as everyone has already said....dreams can come true...it's up to you!!!

Trw, I don't think orange shoes would convince anyone I was warm & fuzzy. 🙂

Sunnyd, I'm with you on using the good china, etc.

I ditto the traffic comment. I steer totally clear of Town when there is more than 3 ships in. I used to live in the DC area which always ranks in the top 5 for traffic. The traffic here doesn't compare but it still took me by surprise. A trip to the airport from where I live is only about 10 minutes (sometimes less) at night or really early morning but can take up to an hour at a snail's pace during the day on a week day.

PS-I witnessed the Frenchmen to Havensite traffic in the afternoon...INSANE! I don't know if it's that bad every rush hour but boy was a long line of cars...