2) kingston to usvi or further south.....
This is the part that I think I may be missing. Does this suggest hiring a delivery crew to take her up the St. Lawrence and down the coast? Since you didn't want to outfit her, I didn't think this was an option. In any event, I think you've missed this weather window, particularly given the lead and prep time. But I have heard of some crazy deliveries!
If your heart is set on this, I think the only practical answer is to put her on a truck and ship her somewhere between NC to FL and then hire a delivery crew to take her all the way directly to Barbados. They may have to stop once or twice to refuel. I think, if you mess around with coordinating a pickup in USVI, by the time you pay for dock space, wait for the right weather window, pay your own island hopping fees, etc, you would have been better off paying the extra time to get the job done.
I am afraid that, by the time you add in all the incidentals (rigging, hauling, trucking, food, fuel, probable repairs, fees, etc, etc), this is going to cost much more than you might think. I say over $20k before all is said and done.
Are you sure it is worth dropping this load of cash? Seems you could lease a boat there.