Last week I had almost exactly the same experience as Matt Asay (see his blog). My Blackberry 8820, which I love, had finally stopped taking a charge without me holding the cord in strange positions. The side were the plug goes in had succumbed to massive re-charges and many drops, bends, and abuses. I was out of luck and power.
I walked into my local AT&T store to find out that my Blackberry was about 45 days out of the maintenance window. My only choice was to buy a new 8820, with Wi-Fi. Then I looked over at the iPhone. My wife has one. Many of my colleagues have switched. I even have moved almost entirely to a Mac at home, so synchronization of my calendar and contacts is a bit jumbled, but manageable through Plaxo (thank you) and my other desktop PC (until I find the right Mac-Blackberry sync software). I even love the web browsing capabilities on the iPhone (can't anyone else do that?).
I went back and forth several times before deciding to stay with the Blackberry. I just couldn't give up the immediate email interaction...yes, I'm an email junkie. In fact, as I was debating with the sales agent my Blackberry vibrated and I received an important email. I was sold again.
I was also concerned about the typing...I'm as fast a Blackberry typer as anyone alive (try keeping up with 100's of emails and dozens of real time group chats on this device each day, you become incredible capable with your thumbs!). This is something I think I'll learn to perfect over time with an iPhone.
But in the end I did not make the switch, yet. I know my time is coming. As soon as the iPhone is released to support Exchange via Active Sync I know I'm likely to abandon my Blackberry for an iPhone. The folks in Waterloo probably don't want to hear that too often, but maybe they'll come out with a new device and change the game again?
No matter what, we win.