You know the best way to leave Vegas with a small fortune? Start with a large one. 
If you’re flying in, you’ve got to take Las Vegas Limousine from the airport. It’s only $4/person to the Strip–you can’t take a cab for that, with one or two people. There’s nothing like pulling up to your hotel in Vegas in a stretch limo.
The best way to eat cheap is to keep late or early hours. The Barbary Coast, for instance, has great breakfast specials for $1.99 from 11PM-7AM. (They cook the bacon just right, too.) There’s also the world-famous late-night steak special at Binion’s Horseshoe–steak, potato, salad, and rolls for only $2.99.
You can save a few bucks at the buffets by going just before they switch over. For instance, I went to the Bellagio buffet at about 10:55, right before they changed over to lunch. They charged me for breakfast, which is about $4 cheaper than lunch. Just get some fruit and nurse it for a while as they get lunch set up.
The cheapest gambling on the Strip is found north of the Treasure Island. There’s a $1 blackjack table at the Casino Royale that’s right next to the bar, so it’s a good way to get ripped on the cheap. (They also have $3 double-deck.) There are a bunch of $1 tables at the Sahara, but it’s a long haul from anywhere else. (It is, however, near the Holy Cow Brewery, which I highly recommend.) There are plenty of $3 tables in the evening at the Imperial Palace, which you should check out just for the cocktail waitresses. (Top-notch.)
For an interesting gambling experience, there’s a Texas Hold’Em tournament (that’s poker, BTW) every day at the Luxor at 12:00. $20 entry fee. If you study up on the game a little bit, and play tight, you might have a good chance.
My personal favorite thing to do in Vegas is to get all dressed up, go to the Mirage, get a drink, and hang out. It’s like the crossroads of the Universe in there.
Have fun, and don’t take insurance.
Dr. J
(PS: It might be out of your range–it was certainly out of ours, but my traveling companion was cleaning up at the tables and being a jerk about it, so it was on him–but I must recommend the Samba Grill at the Mirage. Their “rodizio experience” (Brazilian barbecue) is $28.95, but it is a bargain for the true meat lover.)