I've done this a lot with other countries but not with Jamaica much since I usually book hotels and airlines direct for the best price.........
one of the times I got pretty friendly with the reservationist after a couple emails......
and when I showed up at the resort I was upgraded......
plus I had a free Fruit Basket with Rum etc in it.....
plus she gave me 6 complimentary private dining passes versus having to go to the buffet every night.......
so it does pay all the way around to stay on top of your reservations and be nice to people.........
and a couple other times mi had a free room upgrade for being cordial in the emails.......
it's better to be safe than sorry and worth the extra effort to follow up.............
now if I could only find a way to fly First Class for free.......lol
Cool Runnings, Marko