It generally seems that you dont get taxed too much on your baggage that you check. I came and went at least twice a term, always bringing back the maximum baggage requirement and was only dutied on my laptop the one time. My bags were always checked, but never thoroughly, and if they didnt ask what i had, I didnt offer. However, most people who shipped stuff, esp through amerijet, got dutied out the wazoo. I think they do that bc they know you are shipping valued items, and they are used to going through shipped boxes of retail items for stores and assigning duty to them.

My two cents, which have said often, is dont ship anything down, and fly Air Jamaica instead where you can bring basically everything you want.