The answer is that it's impossible to determine with 100% accuracy,
Ever heard of GLBSE shares? You think it's hard to prove ownership if someone has been scammed?
Your first post in this thread has no mention of GLBSE shares AFAIK, given the Pirate fund has everything recorded with a 3rd party, and the payment is going through and verified by a 3rd party it could be easier and safer to determine the outcome of the bet. Personally, as long as I don't have precise information, I will never put money on the table, but I see a lot of persons are willing to do so.