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Moderati ergo sum
Join Date: Jun 2010
Device(s): Galaxy Note 10.1 (2014), Nexus 4, Galaxy S II,
Captivate, Nexus 1, Nook Color, Asus Transformer T-1
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Sure, you can, and people do this all the time. Here are a couple of things to consider ... The phone's going to be locked to your carrier (AT&T, I assume) and will be listed as a contract phone under your account.
If whoever you sell it to is on AT&T (and plans to stay there) and you maintain your account according to your contract, then all is cool.
Here's how it could go wrong:
You default on your contract. If you do not complete the contract and just stop paying without paying a termination fee, they will deactivate (aka. blacklist) and phone still on contract. The buyer will wake up one day and it just won't work as a phone and they won't have a clue. Unfortunately this is a scam that happens all to often.
The buyer wants to move to a different carrier. In the U.S. there are not a whole lot of options for moving around since all the major carriers do something just a bit differently and make phones incompatible, but I suppose T-Mobile would be an option. To move, the phone would need to be unlocked and AT&T doesn't have to unlock it until the contract is up, even though the buyer bought the phone without a contract, they are still tied to yours.
The phone is lost or stolen. If the buyer would report the phone lost or stolen, you still would need to complete the contract and not be eligible for a replacement.
The phone fails within warranty. I'm not sure what Apple's policies are on second owners, but they may require original proof of purchase or even deny the claim. I do think Apple has a pretty liberal policy about it's devices so that might not be much of an issue. I really don't know.
Let's do the math ...
iPhone 5's used seem to be going for $250 ~ $350 so let's say $300. The 2014 Moto X unlocked is ~$500. The iPhone 6 lists for $650 and on contract is $200. You won't be able to sell it for full list, but probably close so let's say $600.
So you sell the iPhones for $900 and pay $700 for the Moto X and the contract so you make $200 (minus tax and shipping and whatever else you need to pay out) so let's say your net is $100~$150. Seems like a lot of hassle, if you ask me. I can make $100 in a couple of hours freelancing free and clear with no contract.
Personally, I'd sell the iPhone 5, buy the X and be done with it. Then start looking into cheaper plans and you'll be able to save a heck of a lot more that $100.00!