I would look for regular oil changes (preferably synthetic) and other typical maintenance items. Best year to buy is the newest one you can afford, with maintenance records and low miles. Why are you moving from the '96? It would seem that you will pay a pretty steep price to get a 2-4 year newer car with a little more power and have to feed premium fuel. Mind you, I have looked at doing the exact same thing but resale values for used cars are pretty poor. It's a different story if you are adding a car and not replacing one. If that's the case, skip the last few sentences.