Does anyone know if you are hassled if you take out a brand new laptop from abroad - Canada or US to Jamaica or if you have to pay extra etc. It would be hand luggage.

Merely say it's your own. Be certain it works and you can turn it on and boot it up for any customs or security people who might question you. In the US, TSA people often ask you to do that to be sure it's not some device to blow up an airplane.

Never had a problem. They will of course put it through the scanner and I'm never sure if that creates a problem for the computer itself.