Sorry your trip had some snafus. I really try to get non stop flights, even when they cost more since it seems if something can go wrong, it will go wrong.

On the other hand, for a short trip to JA, you could probably get by with toothbrush, change of underwear, t-shirt, shorts and bathing suit. (All of which I include in my carry on luggage.)

As for TSA, Delroy has convinced me that I will never win arguments with them over what is allowed and I should just accept whatever they say. On one trip (not to Jamaica) I had a tube of face cream that was 3.5 oz. (3.4 oz is the limit). I had been through airport security probably 10 times with this same tube without problem, but then in the podunk airport close to my hometown, the TSA agent flagged the tube and said I couldn't take it on board. When I tried to explain that I had taken it on at least ten other trips she simply stated: "I apologize if other Agency employees do not take seriously their duty to protect the United States' airways." Really?

Hope your next trip goes without a hitch.