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I've always just bought new cars (ever since my first, a Pontiac Sunfire). I'm considering leasing my next vehicle. I played around with the configuration and built a VW Tiguan Cross Sport, for example, and with $11,000 in combo of trade-in and down-payment I got $264 (15k miles, 36 month lease, $6k down, $5k in trade), while financing it I got $495 ($5k down, $6k trade-in, 60 months, 0%). At 1.9% it goes up to $520. $495*60/96 (eight years of use) is $309/month. That seems odd — the lease is less expensive. But… the lease only works ONCE with the trade-in, because your next lease, you don't have anything to trade in. So a lease on this particular car with a $1k down payment is $551… which is quite a bit more than $309/month. Now, here's the thing… I was prepared to pay a bit more (and this isn't consider lease termination fees, etc.), but about 75% more ($309 vs. $551) for the second car? Sure, I'll save a little (maybe) or break even for three years… but then I've lost my rolling equity on everything after that. Again, I'm willing to pay a little bit more to get a new car every three years, but how does anyone lease at a 75% surcharge? Am I doing some bad math here somewhere, or something? Should we just keep buying new every eight years or so?