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How feasible is it to upgrade a phone on contract and sell the old one?

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I'm planning on getting the Droid Eris next week, and the only thing keeping me nervous is if HTC comes out with the new "Passion" in early 2010 on Verizon. If this is the case, is it possible to purchase the new phone at full price and then sell my Eris on Ebay?

I understand that I might be out a little more money in the exchange, but I can live with that for having that flexibility. Has anyone had an experience with doing this before and is there anything I should know?
 
I've done this a few times with sprint.

just make sure that you clear everything off of your phone, and be very descriptive of and scratches or loose buttons the phone may have
 
I always do this with t-mobile (UK). By the end of your contract (after 18 months) the original phone will have lost a lot of its value, so replacing it makes a lot of sense. As long as the new phone is on the same network (or unlocked) there is no problem.
 
I do this all the time with my old phones. Just sold a Blackberry 9000 and 8900 on Craigslist when me and the woman got the Droids.
 
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