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if you're seeing 33k at dealership for similar packaged car, similar mileage, condition, etc.. I would figure you would get around 28-29 as a trade-in, maybe 30-31 privately. Either way, sounds like you would definitely get some cash back to apply to the lease.
I've done both and for me, trading in saves a lot of hassle and some expense over selling yourself privately. If you have the time to deal with the hassle of letting strangers drive your car, you could make a little more that way, maybe a grand or two. But if you want to trade it in, definitely negotiate the price of the car without any mention of a trade-in, get the deal you want, then bring up the trade and don't let them play games with the numbers. If you negotiate $400/month, it stays 400 a month. If they won't give you a fair price on the trade, go somewhere else. They'll make money on both cars either way, they don't need to make a fortune on either one of them. Treat it like 2 separate transactions and make sure they do as well...
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