A work permit is not only not the easiest thing to get - its expensive, the fees having tripled in the past 3 years. I THINK its somewhere between $600USD-$1000USD after all is said and done (paying for fingerprints, filing papers, brata and transportation to Kingston a number of times...) - its a lengthy process too. And it has to be renewed every year (or every three if you pay even more money).
I too would not go there "expecting" to get a job. Lots of us have 30 or more years working experience - but in what field? One of the documents they (immigration) can ask for is proof that you can exist on your own there for 3 or more months. I've never been asked but I'm always prepared...
Like I said before Giueseppi (sorry if I mis-spelled) living there is much, much different that your current tourist/visitor experiences that you've had. You really do need to take it one month at a time, developing community and learning on the ground "the runnings" - you can be told here but you gotta "live it to learn it".