It's always hard to give advice on this sort of stuff. Having an older car isn't necessarily the best idea if you have no place to work on it, or the skills to do the work. But buying a new car every two years is essentially tossing money out the window.
My daily driver... is 21 years old. It has it's quirks, and occasionally requires expensive parts... but I am able to do all the work myself. The body has seen better days, but overall is quite strong.
My wife's car is 14 years old. Again, has it's quirks, and the odd expensive item, but it's much cheaper in the long run. I bought it for her two years ago when we were dating... $850 car + couple hours of body work, patching rust holes with welded panels, paint... total cost of under $1200... to replace her newer truck that used more than twice the fuel. Sold her truck and paid off the loan on it.
A huge factor in the costs of repairs is labour; if you can do it yourself, you can save a lot of money. Most recently:
My Car:
-clutch was going (turned out to be the hydraulic clutch master cylinder... swapped in a used spare I had)... replaced the original clutch... 230k km's on it... still date-stamped from 1987, almost worn to the rivets. A weekend to pull the transmission, then pull the engine when I realized it was easier to do it that way. Tools required... sockets, wrenches, hoist (could be done on axle stands for most cars), engine hoist (can be rented... or done with a floor jack). Cost for parts - $400. Labour saved - $900+ from an independant shop.
-heater core - $80 part... 7+ hours to remove/install the dash to do it. Specialized tools... small metric sockets, philips head screwdriver, patience. Labour saved - $800+ from the dealership (dealer quotes 9+ hours and two tech's.)
My wife's car is going to need some minor work soon... I've got a whole spare shift linkage sitting in my trunk ready to have new bushings fabricated for it. Couple new brass bushings, reassemble the shifter, then it's just a couple hours labour to put the car up, drop the exhaust and heat shields, and replace the shift linkages.
My father still has his '98 Outback. One of the few vehicles he's ever bought new. Always treated with Krown rust proofing. Only major work it's needed was a fuel tank... and it will need exhaust work soon. It's been across the country and back without issue. He's had the dealer do the majority of the work on it, and has always been happy with it.
I generally look for cars I have experience with... European cars (older Audi's and VW's), and Ford stuff. My first couple cars were older VW's, then an older Audi quattro. Picked the Ford Escort wagon for my wife because my father owned one (till my sister rear-ended someone with it), and would buy another. Great fuel economy.