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If a car has really good resale value, it's best purchased new IMO. If it has bad resale, used makes sense. Historical examples- why buy a 2 year old F-150 for $3K less than a new one? If you can buy a 3-4 year old Lincoln or Cadillac for 50% of new- good deal.
When you buy used, you have a car with X miles on it that is Y years old. It will always be worth less than a new one would be when you go to sell. The longer you keep either car, the more the resale difference will approach zero. Let's say the used car has 30,000 miles on it. It's due for a major service and probably close to a set of tires and brakes. Plus it could be fore sale because there was some problem with it or it was there was some bodywork done that doesn't show on the Carfax. The chances are higher that you'll get the color and options you want on a new car, too.
On top of that, a new car comes with a full warranty and the Lemon Law protection. Extended warranties are cheaper on a new car than a used one, and the financing is likely better, too. Add up all these things and often times a new car is a better deal than a used one.
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