Re: Prop Bet Question
His roommate is decent and knows what he's doing.
Id say fair would be roommate needs to win 16 holes outright to win the bet, 14 to 16 is a push, and under 14 and pennpal wins. I think you should also look for a match play format like this one and not stroke play because he will not blow up and make worse than a 5 while you easily could.
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