What risks? Just pay them and everyone continues winning and you're earning so much it doesn't even matter.
Also doing this would kill missions again too.
So y'know.
You'd have to be basically a rule abiding griefer to be blowing up all those transports. But I doubt many are gonna do that if anything someones gonna defend the multi boxers and get payed a half sum something similar to what a pirate actually pirating would make. which still isn't going to compare or dent the profits made by a multi boxer whose trading in a line and or claims to be unrelated to his other characters and so on there's just so many holes in this.
What's this meant to achieve? To equal out the economy? Communism? This might as well be moved to flood.