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- Switched from a Sprint flip phone to AT&T for the 3G in 2008
- Left AT&T for T-Mobile in 2009
- Skipped iPhone 3GS
- Bought iPhone 4 in 2010
- Switched back to AT&T in 2011 for iPhone 4S
- Went to Verizon for iPhone 5
- Back to T-Mobile in 2013 once they finally got the iPhone
- Bought iPhone 5S
- Bought iPhone 6
- Will buy the new iPhone every year from now on.
 
iPhone 4 for me and never looked back. I thought the 4 was so amazingly crafted I had to get it.
 
I got my first iPhone on the Verizon launch day. I had been wanting one for such a long time and I knew I had to get it ASAP. Thankfully, I had ignored all of the reps at Verizon saying "Upgrade now, we have Android smartphones which do more then iPhone for free!". I had a dumb phone at the time but had used Android phones in the past and it wasn't for me. I was coming into the Apple eco-system at the time and I was not going to waste my upgrade.

Along with the upgrade, I also got a "New Every Two" discount which essentially made my iPhone $249 before tax (here in CA tax is on the un-subsidised cost, so $60 in tax or so). I went 32GB because I already had a 64GB iPod touch and I knew 16GB would not cut it. Unfortunately, I wanted white and thought that when the VZW phone was announced, white would finally hit production. No such luck so I went with black. Hey, I had already waited years for this phone, I was not gonna wait another 2 months or more.

My dad had already had iPhones for 2 years prior (he got the 3G just before the 3GS came out, got the 3GS full retail, same with his AT&T iPhone 4) and I already had used iPod touches for the past 1 1/2 years so I was no stranger to iOS.

I just remember when I got the phone thinking to myself "Its mine, its finally mine!" I wish I had held onto that phone, but luckily my dad and mom moved back to Verizon from AT&T after their contracts ended. One of those phones was sold, the other is in my collection with its original box. The whole phone was actually just replaced by AppleCare not even a year ago because of a dying battery.

From there I got my white 32GB iPhone 5 (aka the phone from Hell with 14 AppleCare replacements), gold 32GB iPhone 5s (awesome phone, no issues), and white 64GB iPhone 6 Plus (awesome phone!).
 
Got the original iPhone few months after launch. Skipped the 3 series. Then got the 4, 4S, 5, 5S, and now 6 Plus. Never ventured outside the iPhone. Didn't have to.
 
I've had every model since the start with a random HTC Diamond (so so so bad) thrown in there when I shattered my 3GS and my screen started shorting out.
Still have my 3G as an iPod for my surround sound and it works like a very slow charm!
Had an 8gb 2G and thought it was the greatest thing ever made but now that I have a 128gb 6+ it seems like a paper weight! Haha
 
Edge original, 3G, 3GS, 4, 4S, 5, 5S, 6
Thank God for a wife that doesn't mind having the last generation.
 
My wife and I have been exclusively on iPhones since the 3G, and have owned every model. We upgraded every year either because AT&T offered an early upgrade or because we could recoup nearly all of our upgrade costs through eBay sale of the old one. We've had great experiences with every iPhone, and with the support we get at the Apple store. As a gadget geek, I've spent plenty of time playing with Android and Windows models but just don't find those to be a complete and polished package like Apple offers.

The only time an iPhone ever crapped out on me was after I gave my old iPhone 5 to my dad and the speaker failed. The Apple Store fixed it for $100 in less than an hour.
 
I actually worked for Apple retail during the first iPhone launch! And thus I bought an original iPhone. Haven't had any other type of phone since, just because I've grown to love the interface and the ease of getting support.
 
I've owned every generation of iPhone since the original. I've also had a few forays into the world of Android but I keep coming back.
 
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