While you seem to have some industry experience, I think you perhaps write off the iPhone a little too easily. I can certainly see some parallels with Apple's Mac strategy in the 80's, but they have done a lot of things right (from a dev point of view), and are seeing success accordingly. 100k apps and rising speaks for itself really.

I agree that the iPhone has a small marketshare of total mobile phones, however the vast majority of mobile applications (where a web app won't do), are targeted towards smartphones. As you can see on this graph, the iPhone is currently in third place with around 13% marketshare. Not insignificant, and not bad at all for just over 2 years on the market.

As another poster mentioned, Apple has made it very easy to sell and buy Apps on this device, so most people that own an iPhone will spend money on Apps. Contrast this to Symbian where it takes a pretty dedicated and sometimes technical user to buy and install an application.

So, in the "real world" the iPhone is quite a dominant force already. It may yet prove to be a fad, and the mobile industry does move very fast, but I don't think so. I am personally seeing an increasing amount of consulting requests specifically iPhone related, and interest from corps is sky high.

With regards to your Java point; J2ME is nice (sometimes ;-), and it certainly has the largest install base of any mobile language, but the sad reality is that it is nowhere near "write once, run anywhere". For a cross platform J2ME mobile project, you will usually spend at least 50% of your project time porting and getting things running on devices that all implement it a little differently and have their own quirks. So supporting the majority of smartphones (Symbian, Blackberry, Win Mo and iPhone) will require a lot of specialised code anyway (unless you use a cross platform framework, but that has it's own drawbacks).

All iPod Touches and iPhones are essentially the same (barring some hardware differences like processor speed, bluetooth, etc), and an App written for one will almost always run on any other (I have had some obscure issues that crop up between different models, but nothing of significance). This is heaven from a dev's point of view!