Distributing a Windows Mobile application involves putting your CAB file on a webpage somewhere, as opposed to paying for a development license and submitting your software to Apple hoping to be eventually approved for inclusion in the App Store (if you want to be available to the non-jailbroken majority of users.) I don't think that particular comparison is very flattering to Apple.
This is the suckiest part. Paying money (every year!) to develop on a device you paid for is insane. I don't know if any other platform has annual development fees. Damned if I'll pay money every year to be "allowed" to write/deploy code on my own device.
And downloading a windows mobile app involved users putting aside every shred of hard-won suspicion about random binaries from essentially unknown development shops.
Now how about distributing a for-pay app?
How easy was that?
Well, the Windows Mobile model is exactly identical to the established model of trusting, advertising, and distributing any other computer software. I have yet to be convinced that a different model for handhelds is better.
If I had to choose between making development free and easy and making sales and advertisement easy, I'll take the easy development. There are always a lot of people who will create interesting things for free, but many of those people might not feel like creating interesting things in Objective-C after paying for a development license and then not being able to distribute their things if Apple doesn't approve of the thing they wrote.
It seems pretty obvious that your hypothetical objections have not been a problem in practice; no other mobile device has an app ecosystem on the scale of the iPhone and iPod Touch.
I disagree -- I don't know how to find reliable statistics for how many, but there are a huge number of free Windows Mobile apps to suit nearly every need. I have a Scheme interpreter with a little IDE on my HTC phone+, and a GBA emulator for it too. I think that the relatively large number of iPhone apps are a natural consequence of the big userbase and are in spite of their App Store model, not because of it.
