Julie is right, it's all about the maintenance.
I spent about 3 hours a day commuting and my newest car is 2001. My default DD is the 96 Firebird, I've driven that thing everywhere and in the worst of conditions...It's comfortable, practical (decent rear seats, and huge trunk/hatch) cheap to operate, decent on gas and when it does break I can do the repairs myself. It even still gets compliments and attention from random people, just this morning some guy in an older BMW 3-series gave me a wave on my way to work.
With that said, I've owned the car since 2007, so I know the history, and I've kept on top of eveything. I don't think I'd buy a 1996 now as a daily unless I really knew the car. If I needed something now strictly as a DD I'd be looking for something no more than 5 years old and around the 100,000km mark.
Another factor is your own mechanical ability, if you can drive an old car is do alot of the upkeep and repairs yourself, you can save a lot of money. But if you're going to be depending on a dealer or shop to do everything I think you'd be better off with something newer.
BTW: My mom DD's a 1980 MGB, year-round. Again, the car is kept 100% and rarely ever breaks, when it does it can usually be fixed in the driveway with a couple hours and some hand tools.