I haven't been there personally but you may find some useful info on the Jamaica forum. Here is the link for you.
https://boards.cruisecritic.com/forum/67-jamaica/
It could be software issues, hardware issues, less than competent I.T. techs or any combination of those factors. Only they would be able to tell you.
Personally, I haven't noticed constant issues as you reported.
I was just looking at that myself. Google Maps says it's almost 1600 miles, about a 23 hour drive. For me the last thing I would want to do after a nice relaxing cruise would be to get in a cramped vehicle and drive for a couple of days.
This is the test forum. Seems like you are looking for the Roll Call for your sailing. Click on the "find your roll call" link at the top right of this page.
Enjoy your cruise.
Recommend you ask/research on the East Coast Departures forum. Lots of good info there. Link:
https://boards.cruisecritic.com/forum/317-east-coast-departures/
That's not what is being asked. He's looking for the bag drop off area so he doesn't have to carry his bag around while waiting for rooms to be ready. 🙂