"I usually fly to JA on US Air and usually get upgraded to first class while checking in, sometimes from US to JA, and pretty much all of the time from JA to US. I have found that there is a pretty small difference. "
That's because you are flying on US Air, lol.
Really - that was a joke so please do not take offense! First Class is something I treat myself to when flying for pleasure. I fly on airlines such as American (my go to frequent flyer airline) and Air France where the difference between first class and coach is pretty huge. Its the sweet reward for the 30,000+ miles flying all over the country for work, mostly in coach (sometimes if I can in First). Call it my "mani-pedi" - its important to me. I fly so often comfort and ease is a huge bonus.
I come and go about living in JA for more than 3 months. Right now its impossible because of work...my hope always was that as years go by my physical presence would not be required as much on job site as I can and do work from home in Jamaica. I even proved to myself this winter that I can do a business trip from JA and back with no trouble.
I know at this time I don't want to buy anything in Jamaica (see above)...and the reality is my bucket list of other places I want to go and see is growing as I get older. As had been said before, the best laid plans often go fornaught - so the best plan is a flexible one in my opinion - that and not putting off what it is your heart really wants, be it an extended stay in Jamaica, trekking the Himalayas or starting an Emu Farm...
Life is short. Trip hard. That's my "plan" and I know it doesn't burden anyone.