"i hear it all the time, must be nice to stay so long....must be nice to take work off for that long....etc. "
Yup - me too...and my response is always to smile and say, yes. It is nice.
But as far as taking off work for three months - that's not me. I do a little work every day I'm there, I have to. I own my business and the buck stops with me whether I'm in the states or in Jamaica. There are actually days when I'm behind the computer the whole day - the business doesn't stop nor do I want it to. I'm blessed to have an amazing assistant holding down the fort but I still need to keep my eyes on things, pay bills, etc. Going when I go and staying as long as I stay is not random - I go when things are slow in my business and I stay as long as I possibly can before things start to get busy again....the last month I'm there is when I'm usually doing the most work there. As mentioned, this winter I wasn't home more than five days when I had to travel again for work. Last year I "commuted" from Jamaica to New York for that same gig.
As far as the trust fund folks and the alimony folks and the drug dealers - I've been thinking about this and have come to realize that the folks I know that do what I do (staying more than say 2-6 months), none of them are any of these. None...most are retired with pension and money in the bank, others are like me with their own businesses or a very flexible work situation. I've only heard about one trust fund situation from many years back - and I've known of a drug dealer or two who have done this type of stay as well - and didn't know either personally.