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Yeah, that would be a literal nightmare.
I've also seen the person who buys all the tickets end up buying additional tickets for themselves...and the first time the guy did it he didn't clarify which tickets he bought for himself and which were the "pooled" tickets. I swear to god if any of those won he'd claim he bought it for himself and fuck over everyone.
After that first time I straight up demanded that he specifically take a picture of all the tickets that are for the pool and not mix them with his own tickets ahead of the drawing.
...and one time I may or may not have created an excel spreadsheet with all of our entries that autocalculated if we won any amount of money and highlighted the tickets with winnings for easier cashing in. That spreadsheet took like over an hour to make because I couldn't find a reliable "image to text" program that could read the ticket numbers consistently.
So the lottery maniac lives inside me somewhere...