This is most extravagant gambling moment in my life thus far. Right after I checked out of The Mirage in Vegas, I had $200 left to gamble and was even from the night before, and before I left for the airport, I went to the highroller area and played the $100 slot machines. I turned $200 into $1000, from which I cashed out, and ran out of the casino and headed to the airport. I ended up racking over 500 points on the players card, and was even offered free weekend stay a couple months later.
As far as purchases:
Buying an Acura RSX auto w/leather when I was making less than $20k a year, the insurance and car payment were higher than my apartment rent, although rent is
relatively cheap in Arizona.