$ monthly rent x 12 = year

Digicel WIFI as I need it ($4K jmd/30 days)
Cable - basic is about $1800 jmd/month x 12
Digicel phone credit, as I need it
Laundry

One factor in renting is whether or not current and water are included, or will you have to pay your own? Mine is included, and we have proved to be 'conservative users' and landlord is happy with the arrangement. I figure he gets a break on utilities and normal wear & tear when I'm not around. Your utility use will always be the unknown to a potential landlord or, it might be to your advantage to have the accounts in your name. Cold water only is common here, but some places have solar or instant hot water.

Best is to come for a few weeks and look at different places. Rent prices are all over the scale, from about $200 usd to more than $1,500+ usd/ month. You don't want the lowest and probably don't need the most costly. My guess is you can find something nice for less than $ 900/month usd including current & water (you or them), and that's on the higher end (not knowing what 'nothing fancy' means for you).

Commit for 3 to 6 months and find out if you like it to stay on or want to look another place. You can get a decent rate for that length of time, especially if its during low season.

Location affects transportation. Point Village is kind of far from the beach and town, and past Out Of Town Pastry on the west end is beyond the regular taxi routes. West end is very convenient, only 1 taxi ride to grocery stores/town (2 to get to the beach). West end has a lot of local bars/shops/restaurants to enjoy within walking distance, mostly local residents, a generous helping of expats/travelers/backpackers, and some tourists. Tourism is the reason we have so many places to hang out, don't knock them too hard

As jitterbug stated, with some long term rental/living experience under your belt, you will have wisdom and experience on your side when looking for your dream property.