$600 + ($60 x 24) = $2,040

(including minimum two year contract)

So you misunderestimated the actual price.

+ Video player for my commute and travel ($250+).

+ WiFi device for remote admin/reading news ($300+).

+ A good phone that doesn't crash ($200+).

It's the best available option in the three categories I actually want. It's a good deal if you use its features and probably a bad deal otherwise.

We don't know yet that it doesn't crash, or do we? Here's waiting for Rev 2.0...

Look at it as a business expense. I actually am since my software needs to have some good mobile functionality.

But like OS X, the iPhone will still only have a minority share, optimizing for other devices might make more sense. Although the iPhone people might be a special demographics (especially prone to use web applications over the phone).