NO need to convert to USF ..you are losing points on every currency conversion .. cambio is FINE with Canadian funds ..as always ..and especially now that our currency has gained huge on the greenback ..As for the 100,s ..not sure ..but I'd be surprised if it was an issue ..No need to bring too much cash with you .. ATM's are plentiful and dispense in Jamaican or USF ..
The best advice I can give you here is to LEARN the Jamaican currency exchange and use Jamaican as much as possible ... this will save you untold money .. remember be generous ..but more importantly ..be discreet ..