Let’s have some long weekend fun.

As we approach the holiday break (at least here in the US), I’d like your thoughts on the ongoing iPhone vs. BlackBerry debate.  I ask mainly for my own purposes, but I know for a fact there are others out there considering a similar move, so I hope this is useful as a larger discussion.

I use an 8130 BlackBerry Pearl on Verizon right now.  It’s a fine phone, but not without its shortcomings.  I’ve long wanted an iPhone but have resisted the first generation due to a lack of 3G and business-class email, and now that most of my concerns have been addressed, I’m really considering the 3G.

I have some questions, however, that I hope current iPhone owners (preferably those who came from a BlackBerry) might be able to answer.  If I move to the iPhone, I have a pretty clear understanding of what I will gain, but I want to be clear on what I will give up.

So, here goes.  Your thoughts welcome in the comments.

1. The keyboard.  Oft-maligned, it is the sole impediment for a few of my colleagues.  While I know the touch keyboard will never equal a physical keyboard in terms of tactile feedback, how is it day-to-day?  Does it get more livable as time goes on, or does it remain the Achilles heel?  From friends who own an iPhone, I do understand there is a learning curve — which is to be expected.
2. The AT&T network.  Verizon has long touted the strength/reliability of its network as its prime asset, and for the most part, I agree (although, let me tell you, I drop on the average of one call per day given 60-90 minutes of talk time a day).  I spend most of my time in the suburban Detroit area, so I would imagine coverage between Verizon and AT&T would be largely the same.  If anyone else has moved to AT&T from Verizon, what are your impressions of AT&T’s coverage?
3. Non-SMS-based chat.  For chat, it blows my mind a bit that the first-gen iPhone had nothing more than a glorified client for SMS, which might be the most expensive data service on Earth.  On BlackBerry, I use BlackBerry Messenger (direct device-to-device communication) every single day, and it doesn’t cost extra and can transmit media, like pictures and video.  Because I don’t feel like routing all of my IMs atop SMS, what is the most viable workaround that’s not web-based?  (I know about the newly-announced Google Talk for iPhone, but the jury is out on that one, as it still requires a Mobile Safari instance to be active in order to work.)
4. Battery life.  Since the battery is sealed, how reliable has the battery been?  What’s the average charge yield in terms of talk/standby time?  How quickly does it recharge once its plugged in?
5. Reliability.  About once every 10 days, my BlackBerry becomes gunked up internally and decides to crash, forcing a hard reboot.  Other times, I have had to manually pull the battery (a move familiar to all BlackBerry owners) to force the device to reset from a stuck state.  Does this happen with the iPhone?  If so, how often?  What does it take to enforce a reset?
6. Physical size.  The iPhone’s size — for now, at least — is dictated by the requirement to have a touchscreen large enough for multimedia use as well as to accommodate the virtual keypad plus application content.  I get that.  But overall, how does the size wear on a daily basis?  Easy enough to slip into a pocket?  By contrast, my BlackBerry Pearl is downright small.
7. Form vs. function.  What I’ve heard iPhone opponents say the most is that the iPhone is a great UI wrapping a pretty mediocre smartphone, browser excepted.  iPhone enthusiasts say the UI is just the topmost layer of the most sophisticated and well-designed mobile device on the market.  Which is it?
8. HTML email.  One thing I can’t stand about the BlackBerry is that it’s useless for HTML email, which, for me, is about 30% of everything that I get.  Does the iPhone do HTML email accurately?
9. Bluetooth headset compatibility and overall Bluetooth signal strength.  I have two main headsets that I use: an Aliph Jawbone and Motorola H700.  Both work just fine with my Pearl, but the signal range absolutely sucks.  In fact, if I’m wearing a headset and my BlackBerry is in my pocket, I will get oceans of static if I so much as turn the wrong way.  Does the iPhone support full, modern Bluetooth hands-free profiles (meaning: will my headsets be supported)?  How is the signal range?
10. YouTube.  The Pearl does YouTube fairly well, albeit slowly and on a very small screen with a tinny speaker.  Can I assume that the iPhone’s YouTube application is nearly as good as watching YouTube on a desktop computer?  Can I access all of YouTube and not just select clips?

Summary

The pure upsides of the iPhone are quite clear, given that it’s a device based on a web-first design mentality with strong plays in multimedia.  I know the browser is the best mobile browser on the planet, its music capabilities second-to-none, and its video handling unparalleled.  Its user interface is better than what you see in most desktop PC applications.  I also know that with the release of iPhone 2.0, we have a bona fide platform on our hands rather than merely a device.  I sincerely believe the pending explosion of iPhone applications will make the device into something that nobody can compete with — a mobile platform with the virtues of a desktop computer with almost no concessions on its mobile communications side.

The BlackBerry, on the other hand, does email better than anyone.  It’s an email-first device.  It’s meant for data entry and text communications.  Its BlackBerry Messenger is perhaps its most unsung asset, as it enables BB-to-BB chatting easier than anything I’ve ever seen.  Aside from these core strengths, however, the BB falls off.  It’s browser is mediocre at best and its multimedia is functional but clearly secondary to the device’s main focus.

Like anything else, a question of which is better depends on what you’re using your phone for, but you can’t ignore the explicit competitive tension between these two devices.  If you had to pick one for daily use for, say, the next three years, which would it be?