I recently talked a decidedly non-techie friend through the iPhone vs. Android decision process. Her iPod was ready to die, and her phone was antiquated, so she wanted to get one device to do everything. We talked it over, and decided the iPhone was the right answer, since it's the best drop-in replacement as an iPod. Stars sync up properly, etc. Otherwise, if that was less important, but having really good Gmail/Google Calendar/etc. support mattered more, she would probably have gone for an Android phone instead.

What really tipped the balance was a deal where Target was doing a $100 trade-in deal on old iPhones. I gave her my now-unused iPhone 3G and she got $100 in credit toward an iPhone 4. Yeah, it's AT&T, but in Houston their service actually seems to work...