Thanks JFMFT!
That's kind of what I was thinking with how quickly everything changes in the IT field. As of right now, looks like I'm talking it over with the wife on spending the money for a new phone.
Just remember... $319 for a 1-year contract sounds like a lot (and it is), but it's very much made up for by the fact that you can usually re-sell a device a year later for at least $175-$200. You'll make up over half the money you spent up front by selling your old device on Craigslist or gazelle or green.ebay.com/instantsale, and then you can take that money and put toward the price of your next 1-year contract phone.
So think of it this way. If a 1-year contract is $319 on average, and you can get an average of $200 back selling your 1-year old phone online... you only end up paying on average about $119 per year for a phone. Multiply that by two years and that's an average of $238.
Most people spend about $200 every two years on a new smartphone already... but you get the latest & greatest every ONE year for a premium of about $19/year over what it would cost on a 2-year contract. That's a good deal. Comes out to about an extra $1.50/month on average over a 2-year pricing structure, but in the time frame of two years, you get TWO phones and you're guaranteed to be on one of the most new phones on Verizon at the time. It's a win-win for you. And it puts more used devices in the hands of customers, which is a win-win for people who are afraid to sign contracts.
And that's not to say you'll only get $200 for an old phone. Some people on Craigslist are very desperate - they will pay much more than $200 for a good condition used smartphone that's in high-demand.
I have had several offers above $200 for my Droid X last month... but couldn't take any of them at the time because of no official release date for the Thunderbolt. A girl offered me $275 for my phone (didn't even want the SD card... the 16GB... she said I could keep it, lol) a month ago when we thought 2/14 was the Tbolt release date. Too bad she isn't interested anymore, but I sold my Droid X to ebay's instantsale for $241 anyway, so it wasn't that bad.
And that's why you get a case for your phone! Keeping it looking brand-new helps you get maximum value for it a year later when you want to sell it off / trade it in.
Use all the options you have available to you... and don't sign 2-year contracts if you yearn for the latest & greatest.