1. Buy the most expensive or future proof phone that you possibly can.
Doing so will insure that you recieve a fair amount of money when you decide you want a new phone. An example right now would be the Galaxy S2. Pony up now, knowing that you'll receive a fair bit of money for the sum you invested.
2. Decide what to buy. ( The second time around)
Six months later, and the newest phone catches your eye? Look for the phone you want off contract so that you can buy it and the carrier won't care that you have not completed your two year contract. Get a good deal for it, though, and don't get ripped off. Look on Craigslist, but again, be careful who you buy from.
3. Sell your phone on eBay.
One, make sure you sell it on eBay. Don't sell it on Craigslist because you aren't going to get nearly as much money for it. Secondly, set the settings for the minimum price that you want it to sell for so that you can relist it if you don't get the amount you were hoping for.
See, that wasn't so hard was it? Right now, seven month old Motorola Atrixs are going on eBay for 350-400 dollars. You can buy a Galaxy S2 on Craigslist for $520. 520-350 means you are only paying for around $170 dollars out of pocket, a pittance compared to what it would cost if you bought it and kept your phone.
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