Comment Driver (Score 2, Interesting) 130
The game "Driver" might be a good choice. It's got realistic traffic, a damage model that's at least more realistic than most games out there, and a freeform mode that you could put to use for some dry runs before you actually take him out to play in real traffic. You can find it for the PC on most $9.99 racks, it will run on an older machine, and it's been ported to a number of video game platforms as well (YMMV). All this, and it's a fun game, too.
Also, if you don't like the getaway driver/true crime themes of the previous, you might also look for Midtown Madness, which is a racing-themed game with realistic traffic, a freeform mode, and a fairly detailed simulation of downtown Chicago. It might be a bit harder to find, though. Again, a fun game.
