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I've been buying and selling used iPhone, and have gone through all generations, each used a year or more.
(Purchase Price / Sold Price)

iPhone 8GB (250/220) -> iPhone 3G 8GB (200/200) -> iPhone 3GS 16GB (270/220) -> iPhone 4 32GB (250/300) -> iPhone 4S 32GB (400/Now)

iPhone price drops quite fast within 6 months of release, but the used iPhone price stay quite steadily.

And with a good opportunity, you might not spend much upgrading to the latest gadget.
 
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Nope. I just upgraded from 3G 8g to 4 32gb 'cause I didn't want to be left on iOS 4.2.1 :)

I wanted some of the feature in ios5, like NC, reminders, etc. Wanted more disk space, and it was time for something new.

I'm buying on the secondary market, and using the iphone as a ATT. No contract, means no subsidy on a new phone, so I'm in no rush to upgrade.

My general rule is to state a couple generations behind the latest. I might not upgrade to 4S when the new iphone comes out tho'...
 
No. I bought a new 3GS 32gig right when the 4 was introduced. I was disappointed they didn't go to a 4" screen at that time, so I stuck with the more comfortable 3GS. Held on to that expecting a new model (silly me) when the same looking 4S came out. At that point I bought a used 4 off ebay. It's doing great, so we'll see if the 5 warrants a buy.
 
My first iPhone was the 3GS. I've upgraded to each new iteration since.

For me, it's to have the best and greatest. I did that with the HTC windows phones I had previously, too, so it's not just an Apple thing for me.

As others have said, if you keep your current unit in good shape, it's not too hard to sell it and pay or 50-90% of the upgrade cost.
 
Oddly enough I only upgrade every other year, however I'm on my third iPad so far. Strange how that works out.
 
I have since the 3GS. Sold the 3GS for $300 got a 32gb 4 for $299 (Wash) Sold the 4 for the $350 and got the 64gb 4S for $399. so i lost $50 but upgraded to 64gb so it was worth it. Im hoping to do it again when the new one comes out but my upgrade still says like march 2013. hopefully as it gets close the upgrade moves up. my girlfriends line has an upgrade available but she doesnt want my 4S haha.
 
Only upgrade if the model has some new features that I like.
If the Iphone 5 has a nice design with some exciting features I'm in.
 
Ever since the iPhone 3GS. I honestly don't know how I even survived iOS 3 compared to iOS 5. I mainly do it because I love having the best phone in the house hold. Sadly I've never had the full experience where you camp out.
 
I don't but I have a friend who just HAS to have the latest iPhone out. Personally I think that if your iPhone works perfectly why waste money to buy a new one that does almost the exact same thing as the one you have now. But that's him...
 
I got my original iPhone (2G) right at the end of it's shelf life, when O2 (UK) were clearing them out to make way for the 3G.

I kept that until the 3GS came out when I then bought a 3G from someone who was changing to a 3GS!

I then kept that until I got an iPhone 4 on release day.

I've recently got a 4S (got it free from 3), I've had it officially unlocked and I'll be selling that come October (or whenever), buying an i5 SIM Free from Apple and just sticking my 3 SIM on it.
 
I skip the mid-cycle phones. 4S, for example, was not much reason to update if you already had a 4.
 
Up to the present, I've ordered each & every iPhone upon release.

Not because "I must have the latest" but because I'm a true enthusiast that uses all the features offered & enjoys staying current.

In my case I keep the prior phone as a back up, in case the new one gets lost or broken. It's a nice convenience, not to mention the peace of mind it provides.

I usually replace my MBP's & MBA's in a similar fashion, unless I find nothing of interest (rarely) about the newest version.

The sole exception, will be if the current rumor swirling around regarding the possibility of a minuscule increase in the iPhones display. If Apple retains the same width as the 4S, I'll ignore upgrading for the first time. I have zero interest in another small iPhone, especially with a very odd shaped screen.
 
I did up until the 4S. Now I think I'm going to be going every other one. I might be lying to myself.
 
I've gotten a new iPhone every yet it's released. Most I've paid is whatever the subsidized price is. I do that by selling the previous version iPhone and apply it to the new one. It generally works out to pay as if you renew the contract, however since I pay retail no contract here.
 
My operator only started offering iPhones when the 4S came out so I can't say whether I'd have bought each revision or not. My current plan is to not upgrade to this year's model, but I may be swayed if the hardware is fancy enough :)
 
This may sound weird... But in 4 months time when I'm eligible for an upgrade I'm going to use my iPhone 4 case-less until I either break it or get completely sick of it, and then I'll upgrade to the next iPhone.
 
This may sound weird... But in 4 months time when I'm eligible for an upgrade I'm going to use my iPhone 4 case-less until I either break it or get completely sick of it, and then I'll upgrade to the next iPhone.

Doesn't sound weird. It sounds like common sense.
 
I upgrade phones every 6-9 months or so, I usually buy an iphone when it is redesigned but I do not buy the same iphone redesign twice.

If I have a iphone 3g I don't get an iphone 3gs and when I had a iphone 4 I wouldn't buy the iphone 4gs. Instead I get whatever else is better on the market and what I want/like.

There is a 85% chance I will buy the iphone 5 but it depends on the timming If I don't want to wait I will get another android
 
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