I had to chime on this one as well. It seems like not much has changed since I was doing the monthly trip to JA. I always used a hotel also (usually the one he worked at) and if they questioned why I had 2 suitcases I would tell them my husband and kids were coming in a few days!
Never had hassles, but 6 years ago the computers were not installed yet and I used a drivers license and birth certificate thru customes, so there was not stamps or anything.
Just keep your eye on the weather, here and there, you should be fine, talk to the airline about what happens if hurricane comes, numbers to call(but they don't always answer!!!)etc.