I love this hypothetical. In a "Groundhog's Day" universe that you don't escape until you win the WSOP Main Event, how many tries would it take you?
There are so many variables to break down.
So basically, let's say you play the first time and last 100 hands until you bust. When you wake up the next day, you have knowledge of those first 100 hands, but hand 101 is completely unique to you. So if you take notes the first time through, you can win a ton of chips to set you up for your next attempt.
So you do attempt 2 and play perfectly, Postle-esque (because you already know the outcomes of the hands) but then on hand 210 you get aces vs kings and lose. You no longer have this mega-chip stack and you bust out on hand 300.
You now have the start the grind all over again the next day, from hand 1. Keep in mind, while your opponents don't know they are in Groundhog's Day, you do, which is fucking EXHAUSTING. Remember who crazy Bill Murray starts going in the movie? That'd be you, every day, sitting down at a 10 handed poker table. You'd hear your opponents tell the same stories every single day, like Ned Ryerson.
But at the same time, by attempt 3, if you study your notes, you should be in very good shape. Mind you it's an 8 day tournament, but if you get a huge chip stack going into day 4, you hopefully won't have to play for stacks.
Deep in the tournament when you are in uncharted territory for the first time could get rough. Remember, you need to WIN to get out of the sim, so you can't take your foot off the gas and coast. Going 8 days, 12 hours a day, and then losing at the final table would be torture. You'd then have to wake up the next day and start from hand 1 AGAIN. Talk about demoralizing.
And mind you, there are weird things that could happen in between. Say you play too good. Like you call off for stacks with 5th pair on a KQJddd board with pocket deuces...people will start wondering what's going on. You don't want to put too much focus on yourself- you have to remember nobody else knows they are in the sim so the tournament director/other players will see something suspicious which could possibly lead to you being disqualified. And then you have to start all over again.
So what's the number? And remember you have to WIN. I think it's somewhere between 5 and 8. I think that last part about making sure you don't do anything overly-suspicious, especially the deeper you get, is important. You can get away with a lot early, but let's say they move you to a featured table with cameras, you can't be looking at your iPhone notes anymore. Throws a whole new wrinkle into it.
We discuss this, Darren Rovell's terrible poker hand, the 'rona, Phil Hellmuth not believing in GTO, and more on today's new episode of Cracking Aces.
PS: It would take Rovell 5,000 attempts.