For the last four years Windows Mobile has been my operating system of choice. I switched from Palm after the horrors of the Tungsten T|5 and accepted that whatever bugs Windows Mobile introduced they couldn't be as frustrating as the Palm had been.
Since then I have had a number of Windows Mobile phones (XDA IIi, XDA Mini S, HTC S620, T-Mobile MDA Pro, T-Mobile MDA Vario 2, HTC Advantage and HTC S730) and I think I've reached the stage where I feel the same way about Windows Mobile now as I did about Palm when I jumped ship.
All the devices I have listed above have had one problem or another (except the S620, however as a 2G phone doesn't meet my needs any more). The Vario 2, which has been my daily phone most of the last 18 months, has been the one that's finally pushed me over the edge.
Firstly the inherent problems: the video drivers are inadequate to playback video, TCPMP needs to use the WM software driver otherwise the screen corrupts completely. Which introduces problems with audio synch, as the video lags terribly.
Windows Media Player is plain awful too. Why when you fire up WMP does it automatically default to the internal memory for the media library? You couldn't use it for storing media and there's a perfectly serviceable micro-SD slot for exactly that purpose. And whilst the slot itself is perfectly serviceable, WMP's handling of it isn't and it will regularly refuse to recognise the existence of the card or a library of media files on it, even when the rest of the OS will quite happily talk to it. Worse still, if you choose shuffle and repeat for your music playback WMP plays the list through once and then stops. Aaargh!
The phone side of things isn't to pretty either - radio reception is well below average, completely losing its signal in areas where other phones hang on; and worse still when you come out of a zero reception area back into good coverage it can take an age to rediscover the signal. On occasions the only way to get back online will be to reset the phone.
Browsing via a 3G signal can be hit and miss too. Regularly the phone will fail to make a data connection, despite showing solid signal strength. The only way out of this is to reset...
Are these just the result of me having a bad phone? Unlikely, as I'm now on my fourth, having had numerous hardware issues to add to the other troubles.
Just before purchasing the iPhone I had a chance to play with the new Touch Diamond. And while its a nice clone of the iPhone way of doing things its still Windows Mobile underneath, as I discovered when it managed to crash heavily during my short trial.
The problem is, I feel, that Microsoft's updates have made things less stable, not better and this is in part due to the numerous different form factors and variations that the company is trying to support. Instead of ironing out bugs each update tries to do more and introduces more problems.
Unfortunately for Microsoft people aren't prepared to miss calls or be stuck incommunicado just because their OS hasn't be properly tested. And mass desertions to Symbian, Blackberry or Apple are likely to be the result unless Microsoft get it right with Windows Mobile 7.