I have a friend who has a rather interesting philosophy about buying cars. Right--never buy new. This friend, who is a mathematician, researches what cars have the highest warranty labor rate. This is a figure used by the car companies and it basically tells you how much in repairs the car manufacturer has to pay out while the car is under warranty. The higher the rate, the more trouble and expensive the car is to own. So what you want is the lowest warranty labor rate cars.
He keeps a list of the cars with the lowest warranty labor rate and then he constantly shops for cars from that list. He drives them about 10k miles and then sells. Consequently he is always in a fairly late model car with low maintenance expenses.
Hey, it's not my thing (it would drive me bats to be constantly shopping for cars) but it is an interesting, intelligent approach to the vehicle issue.
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Cher