One Word: ActiveSync
I've been using MS Operating systems and software since the early versions of DOS. I'm currently running Windows XP Pro SP3 on a Lenovo laptop, ActiveSync 4.5, and Windows Mobile Pro 6 on an HTC TyTN. With one exception, I think I can safely say that I've wasted more time and run into more frustration installing, configuring, and using ActiveSync (especially with Bluetooth) than I have with any other single piece of software. (The exception was a bug in some version of Word for Windows 3.1 that caused AutoSaves to wipe out section formatting -- a terrible thing to happen when you're trying to get a lengthy, complex technical report out before a deadline, and very hard to figure out on your own. If memory serves, Microsoft fessed up to the bug about a month later.)
These are just a few of my peeves with ActiveSync:
* You must use ActiveSync on XP (or the equivalent Vista utility) just to read a WinMo phone as an external storage device. No ActiveSync on XP => no transfer => no conversion => no use of your data in other applications or hardware. (This is an unacceptable vendor tie-in, hopefully to be addressed by the Obama administration's revival of antitrust enforcement.)
* You must use Outlook on your computer just to back up your PIM information, such as contacts. No Outlook => no transfer => no conversion => no use of your PIM data in other applications or hardware. (Another unacceptable vendor tie-in; ditto for the antitrust enforcement.)
* The onscreen prompts and help for establishing an ActiveSync connection via cable are poor.
* The onscreen prompts and online help for establishing a Bluetooth connection are exceptionally poor (admittedly aggravated by the fact that my Lenovo has a proprietary Bluetooth utility, forcing me to adapt standard third-party tips and instructions). I eventually figured out that the six-digit pairing code the computer displayed was not the code I was supposed to enter on the phone; that the small blob on the subsequent computer screen was in fact the lower-left corner of an "invisible" code-entry field; and that I was not supposed to check my phone for the correct code to enter, as the computer prompted me to, but simply to enter the same, random four-digit code on both the computer and the phone. Most of the blame for this probably lies with Lenovo's Bluetooth utility, but the WinMo Bluetooth prompts and help weren't much help either.
* ActiveSync on the computer displays only one COM port as available for Bluetooth. The phone refuses to assign that COM port to Bluetooth. Third-party tips suggest that I can manually reassign COM ports on the computer by choosing a different HAL in the BIOS -- at the cost of giving up standby functionality, which is not very appealing on a laptop. Other third-party tips suggest that I can free up the denied COM port on the phone by hacking WinMo's registry. I'm prepared to give this a shot -- but I really shouldn't have to. I'm moderately computer-literate; what is an ordinary consumer supposed to do?
My conclusion? WinMo and ActiveSync have been out for years, have gone through many versions and updates, and can still be extraordinarily frustrating and dysfunctional. (Don't believe me? Do a Web search for "I hate ActiveSync". I'm far from alone.) Android has been out for, what, a year and half? And it's been open source for half a year? I don't doubt that it's still half-baked in many ways, but in light of my experience with other Google products, I wouldn't be surprised if Android outstrips WinMo in stability, functionality, and ease of use in the not-too-distant future.
Just a voice from the loyal opposition...