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.
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. 🙂