I actually thought Apple would have had the better success with a smart watch than most other vendors, as in if any technology company could get the jewelry status symbol angle right, it would be them.
And I suppose looked at relatively that could be argued is the case, as their watch sales are a bit higher than the others lacking that angle.
But the problems with the current crop of smart watches run much deeper than just Apple, and spans pretty much every vendor making general purpose smart watches.
The only real successes are the devices primarily targeted at primary purpose. Think along the lines of the FitBit.
But at least from the point of view of companies like Apple or Google, those target markets are way too small for their tastes, and even without that the expectations of such companies are significantly higher.
As far as the iPhone went, I could see the potential of such a device made well even as far back as the first gen.
My first iPhone however was still the second (or maybe third?) gen, with the 3gs model, and after the application model was in existence for a time. The concept of nothing but webapps just wasn't the right way to go before that point.
Even so there was a window of time when it was clear the iPhone was going in the right directions that Windows CE and Blackberry just wasn't willing to go yet desperately needed to somehow.
A handheld general purpose computer with a phone built in to it was a great concept to start with, but what was desperately needed was a user interface designed around the limitations such hardware inevitably had to have.
I may not have agreed with all their choices, such as an on-screen keyboard which have all traditionally sucked so bad as to be useless (which even now is only a partially overcome problem), and choices such as locking the system down so much as to no longer be fairly called a general purpose computer (which I still very much disagree with.)
A jailbroken iPhone 3 or 4 however was practically my dream come true for such a device.
But sadly when Apple chose to fight against all of the advantages brought about by jailbreaking instead of embarrassing the concept and providing a better way to give us the same features, the writing was already on the wall, and things have only gotten much worse ever since.
Between Apples lockdown of their platform and fighting back against the user doing with their property as they wish, and Googles UI being so ugly clunky and bad to work with, I've no idea what I will be doing for a phone in the future once my iPhone 4s dies completely. If anything :/