Yes, you’re a large dog to win a tournament with $100 if there are $60k chips in play. But that doesn’t mean that it’s a losing proposition, because the prize of the tournament is considerably larger than the entry fee. So even though you fail to win the tournament more often than not even with 100 tries, you win much more than your entry when you do win.

And the example you gave where you’re playing $100 vs. $59,900 heads up destroys the point of playing short stacked. You only get the advantage of a short stack in multiway pots.

the good thing about losing is that you get 100 rebuys at the tournament. so assuming that one of your opponents takes all the other opponents chips over time, and chances are you get stacked, you will be playing against him heads up $59,900 to $100. If I did my math right, that means you need to win 9 all-ins in a row to defeat your opponent. Assuming both opponents are of equal skill, and each all in on average we win 1/2 the time (to the ninth power), we would have odds of 512:1 to taking all our opponents chips. with only 100 tries, this would be losing.

Let me know if my math went wrong somewhere since I’m tired and could very easily have made a mistake

Guys often won’t take free cards in this situation and instead will opt to make these small bets with draws and weak made hands. I wouldn’t necessarily say it’s a good strategy, but people do it all the time.