I didn't vote but I have a different idea.
Rather than transferring cargo and ships via AI why not get a player to do this?
It could work something like this.
You make a contract to transport some cargo from A to B
I would buy your cargo from A and sail it to B
on arrival at B you would buy it back at the sale price + 20/25%
If I get intercepted and sunk or captured on the way I would lose my ship and my money and you would lose your cargo, so the risk is shared.
This would work the same with sending ships.
There would of course need to be some mechanism built into the game so that once a contract has been issued and accepted neither party can back out of it to ensure players are not using this as a way of selling their good or indeed getting goods on the cheap.