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I knew this would happen. As time went on and details emerged, my prediction of how miserable it’s going to be trying to buy an iPhone is going to come true.

You see, now that AT&T is wearing the pants, it’s doing it’s usual business of making things as complicated as possible ensuring that it’s making as much money as possible and making your job as a consumer as difficult as possible.

According to a few sites, including Engadet, there are a few different prices for the iPhone depending on your situation.

• iPhone 3G will be available for $199 (8GB) and $299 (16GB) for iPhone customers who purchased an iPhone prior to 7/11, customers activating a new line with AT&T and current AT&T customers who are eligible for an upgrade
• Existing AT&T customers who are not currently eligible for an upgrade discount can purchase iPhone 3G for $399 for the 8GB model or $499 for the 16GB model. Both options require a new two-year service agreement.

So how do I know if I’m eligible for an upgrade discount? Who knows. I can guarantee that the dude at the AT&T store is going to do everything in their power to make sure I pay the full non subsidized price. That’s been my experience for the past 6 years (starting with Cingular and now AT&T). I would sometimes even bring printouts from the AT&T website showing the price of a device with my corporate pricing etc and they would ignore it and refuse to sell to me.

So this begs the question. How are the Apple employees in the Apple store going to know how much to charge you for the phone? Are the tapping into the state of the art AT&T Siebel Customer Database? I don’t think so.

I think this pretty much ensures that I’m going to go to the Apple store to get my iPhone because I’m betting that the Apple employees are going to be more motivated to sell me an iPhone and get my but out of the store. But really, I’m not sure how this is going to work out.

In fact I am 100% certain I am not eligible for the upgrade price. How do I know this? Well I logged on to my AT&T online account and clicked “Upgrade Phone” and it told me:

Not sure where it’s getting the 04/15/2009 date. Apparently a number of factors picked a pretty arbitrary date. All I know is 04/15/2009 is > 7/11/2008 and that’s all I care about .