Well, I recently installed Test Drive Unlimited for the PC. You get all of Hawaii to cruise around or race in, and you earn money from races and wagers while visiting dealerships around the island and purchasing vehicles and homes.
I earned my first $100,000 and was determined to buy a Cadillac XLR-V. I set my in-game GPS for the 25-mile journey in real time (at 140mph). During that drive, I spent ALL $100,000 on speeding tickets, payment for other people's vehicles that I damaged, and then ended up spending time in prison because I ran out of money to pay fines. (It makes you count down 30 seconds while the camera pans over the police station).
I eventually made it to the Cadillac dealer and test drove the XLR, but I couldn't afford to buy it.

