(Samuel Becket: http://en.wikipedia.org/wiki/Waiting_for_Godot)
I am passionate user of the Windows Mobile devices, but recently, I had oportunity to use iPhone, so I have something to say on that subject:
In the mean time iPhone 3GS is coming, but HTC Hero and Samsung Omnia HD (WM 6.5) are very, very close to the "consumer" experience of iPhone. On the other hand, iPhone is lacking the "Pro" experience like: real good Outlook Mobile support on WM platform - for example: you cannot even put High priority on the message, or folders in mailbox are always collapsed, you cannot edit word/excel documents.
In general, iPhone is making progress daily, for example with version 3.0 of OS it is supporting Copy&Paste (event this is BETTER on WM), MMS, sending contacts and Internet Tethering.
The last one is working great, but some of the Telecom providers are turning it off (which is not the case with WM).
One of the worst thing on iPhone (if you consider Enterprise market) is Custom Application deployment - it is only possible using AppStore, while you can choose your way with WM: you can deploy it directly - by using Active Sync, media card, or download CAB directly from the network drive / Internet.
Windows Mobile Marketplace is still limited to the small number of countries (we will talk about this at http://www.mobilitydays.com/ conference!) and there is problem with "paying for the test account" as my good friend Bernard Katic, MVP told me.
At the end: support for the car hands free is very, very limited in iPhone 3G and there is no support for voice initiated call (by pressing button on the steering wheel of the car) like there is on so many WM devices. I will follow-up when I receive iPhone 3GS, because it (should) have other very important things for me: shooting videos and voice dial.
Other things that are SO BAD done on iPhone are: lack of support for (usable) GPS applications and support for Microsoft Unified Communication platforms (Mobile Communicator) that is supported by WM. Even Skype is working better on WM, and this is because of multitasking (running more applications at once!) that is NOT working on iPhone.
I can add to the list of the bad things following: we have 9 iPhones in the company (so this is NOT isolated case): iPhone often "stops" working for a while (there is some kind of a glitch) and on several occasions (before OS v3) it needed to be hard reset to continue working. On 2 occasions we could not turn it off or reset it - we waited battery to run out - this never happened to me on any WM device!
Only if Windows Mobile 7 will be (better) in supporting multi-touch natural interface (we are expecting even better experience!) and do everything with larger fonts (screens) and support regular updates - Apple showed that IT IS POSSIBLE J and I am (in a second) back on WM platform!
If you are in Zagreb on September 10th, join me at www.mobilitydays.com conference and we can debate some more :-)