I love finding deals, and sharing them with others.
Here is a gift for you iPhone junkies. This is how to always have the newest, freshest iPhone availalbe, without wasting a bunch of money. In fact, it will barely cost you any extra money at all. Of course, just by owning an iPhone you are paying a wireless company a ridiculous amount of money.
1. Check your availability for upgrade. Check it often. Get all OCD about it. Here's why: you will be eligible for a phone upgrade well before your 2 year contract is over. The cell phone compaines (AT&T, Verizon, Sprint) want you to remain a perpetual customer, so they will offer you an upgrade before your contract is up. When you excercise the option to upgrade your phone, it extends your contract for another 2 years.
2. Buy the new iPhone as soon as it comes out. Be an early adopter. I know you don't need the newest iPhone, but buying it immediately will payoff for you in just a few days. Here is how. This of course assumes you are getting it at the discounted price, because you were eligible for an early upgrade. If you aren't eligible, keep checking, because they don't tell you you're eligible right away. Let's say you go top of the line, and get the biggest and best iPhone, with the subsidized price, you'll spend $300.
3. Once you get the new iPhone and activate it, your old iPhone is now contract free! This means you can sell it to someone as an "unlockable" iPhone. This is a big deal. A new, non contract iPhone costs about what it costs to actually make an iPhone. A lot. $600+, depending on which country you live in. So if you have a relatively new (less than 2 years old) iPhone in good shape for sale, you can get $300-$400 for it. That's roughly the same amount you spent in step 2 to get a brand new subsidized phone. BAM! You just upgraded your phone for $100 or less.
4. If you sell it on ebay or craigslist, be careful and make sure you know what you're doing so you don't get screwed over.
I've done this numerous times, and have several friends who have as well. That's how you keep with the latest and greatest without spending irresponibly.