Quote:
Originally Posted by schickel
Looking at the cummulative probability quoted in the thread above, it looks like I was really fortunate that I didn't get myself in a really deep hole

Fairly fortunate. If you play through this person's "straight" method for 103 days or until you win, you win with probability 64.48% with an average net winnings of $265.95, while you lose with probability 35.52% with the whole $1990 gone. Overall expected winnings are $535.27. The probability of winning three times in a row, as you did, is 26.81%.
The expectations assume a prize of $500, as at the link. Your prizes were of different sizes, averaging slightly higher ($520); depending on how these numbers are determined the expectations will vary, but the basics will be the same.
Quote:
Originally Posted by schickel
I should quit while I'm ahead, huh?

Yes. Each additional game you play causes you to lose money, on average.