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Find the new car you want and negotiate with the dealer. Get a couple quotes without your trade in and then see how much equity they give you towards your next lease. This is what I did on my last lease (18 months ago). Thinking about doing it again but going to wait for the 2015 models to roll out.
If you lease a Subaru in Colorado, you pretty much are guaranteed $2-3K of equity at the end of the lease. It's a no brainer if you don't keep a car for more than 5 years.
Can you only sell your lease car near the end of a lease or this is a good strategy to get out of a lease without penalty, say you want another car when you still have 2 years to go on your current car or you need to relocate to a different state and don't want to take the car with you?
I traded in a lease at month 10 (36 month lease) with 11k miles. Dealer gave me "$1,000" of equity towards my next lease. Just a numbers game, but as long as I don't write a check and walk out with a new car with same payment, doesn't matter to me. I treat my car payment as a budget line item, just like my mortgage and entertainment funds.
If you get a great deal on a car and it's in high demand, you can usually break even after 18 months or so. Just depends on what your buyout is and what you can get for it. I'm currently at month 18 on a 2012 Sonata 2.0T Limited lease. I put $0 down on it (well, $1000 from the equity, but not real money) in April 2012. My buyout is $20,000. Car has 22k miles and in mint condition. I could probably get a dealer to buy it out to break even or very close. Who knows. Almost all leases have a disposition fee, which will have to get paid. I think it's around $400 for my Sonata.
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