Okay, now a serious answer:
Do you play this game?
No, because the expected pay-out each round is $3.50, which is less than $5.
What is the probability of making money from this game?
That doesn't seem like an easy question, but we if agree the player will quit as soon as he's ahead on money, then I know the answer is > 0.5
The probability he wins on the first roll and quits is (1/6).
The probability he doesn't but wins on the second and quits is (5/6)(1/6).
The probability he loses twice, then wins and quits, is (5/6)^2*(1/6).
The probability he loses thrice, then wins and quits, is (5/6)^3*(1/6).
In each of those scenarios, he makes money.
They have a combined probability of about .51775.
There are other ways for him to make money, but after he loses 4 times it gets harder.