Sweetness' suggestion of Westender is a good one but again, if you've only been to the cliffs once on vacation you might want to explore the area a little further. Also living at Westender you might need a vehicle, its pretty far south. Not sure where you will be working but you'll need to take transportation costs into consideration as well.

I don't think Sue rents long term. I'm sure there are other options on Westland Mountain Road. I just read on another board that someone rented a 1 bedroom place on that road in the price range you are looking for.

Be aware too that living in Negril "proper" will up your rent expenses. You might want to take a look around Redground or Orange Bay (if you have or plan on having a vehicle).

Another suggestion - see if your employer can't help you out in finding a place. I see that you are planning a trip in October for 2 weeks - see if you can't extend that to 4 weeks. I strongly suggest you spend extended periods of time on island, staying in and around where you think you may want to live to get a true vibe of the place, a vibe you can't always get in a two week hotel-based stay. Instead of being "around" the community, dive "into" the community! Both Jamaican and expat - you will be so rewarded!!

You can do some of this online - do a little Google research and you'll find other forums where the participants are actually living there or have lived there for more insight and community development.

As far as the work permit, oy! There's a lot of paperwork to fill out - they will want to do a background check for criminal records in the US and you will need to be fingerprinted. I'm sure they will require paperwork from your employer as well. At first you might be looking at 2 or 3 trips to Kingston - you can get fingerprinted in Sav La Mar but need to deliver them yourself to Kingston. A private charter to Kingston can cost about $100USD and its about a 4.5 hour drive (or longer, its been a while so I forget). Everything costs, everything! Like I said before, it'll run somewhere between $600-$1000USD. Hopefully your employer will either help pay or pay in full.