I’d used a BlackBerry for about a year and half before switching to an iPhone 3G in late July.  This was just a few weeks after its plentifully-hyped launch, and before Apple started making its first firmware updates.  Being a dork, I had become very familiar with the BlackBerry, even running some handheld training at the organization for which I work.

I’ll start off clearly: one device is not superior to the other.  There are going to be tradeoffs, so your decision should be made based on how you use your device.

Someone who masters a BlackBerry and stays with it:

• …can type an e-mail without looking down.
  Muscle-memory can take care of letting loose a few sentences without really paying attention to the keyboard.  An occasional glance at the screen to make sure you’re on track, and the words are going to just fly out of your thumbs.  I had become so comfortable on the keyboard that I would type out messages as if I were at my desktop, as long as I didn’t need to look anything up in order to respond.
• …can use keyboard shortcuts to navigate quickly through lists of messages.
  A few keyboard shortcuts can make dealing with e-mail a quick procedure.  You can find messages quickly, and file things away without much hassle.  My boss says filing messages on the BlackBerry works better than Outlook, and it’s true.  The procedure is a lot easier.  The BlackBerry is really good at managing e-mail, as long as you take the time to learn to use it.
• …do not need to make compromises on call quality or battery life.
  BlackBerries have evolved to the point where they make pretty good phones.  Battery life starts out at about a week for normal use, to a few days with heavy call volume and Bluetooth activity.  One is fortunate to make it 16 hours without needing to plug their iPhone in or turn it off to preserve a few milliamp-hours to make an emergency call.

Then again, if you want to stick with your BlackBerry, you:

• …should be comfortable with sending and reading only plain-text messages.
  The iPhone renders HTML mail beautifully, with few compromises.  The small screen means you don’t always get an easy reading experience with newsletters, but it is really easy to zoom in to a particular part of a message.  BlackBerry users are stuck with plain-text versions of e-mail until the OS 4.5 update is widely available, or users upgrade to a new BlackBerry, like the Bold.  This shouldn’t be too long, but some users may be held up, because the IT folks are going to need to upgrade the BlackBerry Enterprise Server to support HTML e-mail.
• …can give up hope on navigating the web effectively.
  I am absolutely serious here.  Given all the drawbacks of the iPhone, you can pry it from my cold, dead hands.  Having a competent web browser with a fresh input methodology (multi-touch) has got to be one of the coolest and most useful things to have at your disposal–at least for a dork like myself.
• …will miss out on the App Store.
  There are some problems with it now, but put simply, there are lots of really cool applications that take advantage of the iPhone’s hardware.  These are only going to get cooler as time goes on.

Sometimes I miss the ruthless effectiveness of a BlackBerry as a device to keep my e-mail in check.  However, given my experience with the iPhone, I don’t intend to switch back. Its drawbacks are manageable.  I’ll write up the habits I’ve developed to stay happy with the iPhone and link to that post when it’s ready.