Hi Copper - how cool that you are working towards your dreams. You said you started going to Negril 12 years ago but have you done any long term stays yet. I always recommend this so you can start to experience what it is like adjusting out of vacation mode and into the culture. If you have then you have no doubt talked with those who have successfully made a move there and had a job there as that knowledge is critical also. The other advice I have heard over and over is that you should have a large emergency fund to fall back on or it could become unexpectedly difficult.

I would recommend checking with the Westender Inn. They have some awesome cabins for rent that are basic but cute and affordable (not sure but seems they were around $700 mth but you would have to ck with them to see). As a solo female please make security your prime requirement wherever you choose.

There is also a special Board on the Negril.com Board Forum page that has many threads on "Living in Jamaica".
You have started the first few steps (dream, plan, research). Bless your journey!