What do you use for you primary email and spreadsheet programs?
If you use Outlook, Excel and Word I think the Windows Phone has a huge advantage over Android and iPhone. Those other devices can handle those programs, but the implementation isn’t nearly as seamless and it takes tinkering.
If you use Google Docs and GMail then Android is probably the way to go. Though the iPhone is actually pretty Google friendly too.
Since many of these devices are pretty interchangeable and many of those tools have apps that work on all the popular platforms (to varying degrees of success) it’s often music that can be the deal breaker. For some people it’s all about iTunes. If you are a iTunes user already and like it and are chained to it by a bunch of content it’s tough to argue against the iPhone. Some people, like me, hate iTunes with the heat of a thousand suns and would never use iTunes even if I were using a iPhone and are therefore pretty eager to use something else. For us the Window Phone is pretty tough to top. The Android devices are really, really crappy music players compared to the others. Supposedly Google is working to improve that with the next major release, but that’s always the rumor. If music isn’t something you’d ever use then Android is a pretty reasonable choice and it’s app store is probably going to grow faster and always be more versatile than iOS.
Like I said, I think that the phone that best replicates the PDA experience today is the Windows Phones. It’s well behind the others in terms of apps and it’s a newer operating system so for tinkerers it’s the worst choice. If you want something that just works out of the box with the least hassle, then it’s either iOS or Windows Phone depending on which ecosystem you are already invested in (iTunes, Zune, Hotmail, MS Office etc.). If you are a Googlephile and really want a swiss army knife of a device that doesn’t do music worth a damn and isn’t likely to get timely updates then Android is for you.
It hasn’t really been mentioned yet, but how important is a keyboard? PDA users are pretty used to not having keyboards in general, but the days of the stylus are gone. Do you think that a transition to a touchscreen will be a problem? If you think a keyboard is a priority then that rules out Apple devices and cuts Windows device options down to a few.
I should note that if all you REALLY want to do is have a good phone, a good email device, a good calendar and a good contact list a Blackberry is probably the winner. Blackberry’s mop the floor with all three of the other OSes when it comes to being a phone/email device. It’s really not a competition. Blackberries are much more stable, durable and have the best battery life too.
Blackberries struggle a little with spreadsheets and office stuff, but that might be improving since they’ve updated the OS and gone to bigger screens. Blackberries are useless for music and games, even worse than Android as far as music goes and they have very few apps and aren’t very customizable. The keyboards on Blackberries are phenomenal. However, Blackberries don’t sync in the cloud nearly as nicely as the other products do and are much more self contained than the other devices. iPhone and Windows Phone do a pretty good job of marrying with your desktop and allowing you to take work and life with you from place to place. Android is trying to live in the cloud and doesn’t like playing with your computer, the Blackberry likes to live mostly on it’s own.
Lots to think about.
The best PDA replacements are Blackberry and Windows Phone. Each has serious pros and cons. The iPhone is much more of a media device and a toy, but it’s the most mature and doesn’t really fall flat in any one area but it doesn’t really excel at what PDAs do either. Android might have the most potential functionality but it has the most potential headaches too.