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If you're starting fresh, I'd buy a 3GS. No sense in buying year-old tech when the latest and greatest is only $100 more.

If you're upgrading, it's a whole different situation. If you're eligible for the lower price-point it might be worth it for you, but if you order now you most likely won't be eligible for the new iPhone in 2010. If you're NOT eligible it makes it even harder as you'll be paying $200 more.

For me, there wasn't enough of an upgrade. The $400 was better spent else where. Next year I'll pay half the price for something even better.
 
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