I certainly thought the c. 2001 PDAs under the PocketPC brand were absolutely sick. My hot take is that if the US telecom industry had by that year built out a network of good 3G coverage, those PocketPC devices would have of course had cellular capability, and would have sold like hotcakes, and would have become the basis, the ‘trope originator’ if you will, for Mobile computing. What iPhone was in our timeline.
I think what really held them back was that Wi-Fi was only starting to roll out, and outside a hotspot area, the universe of things you might do with one was necessarily quite self-contained. It limited what “killer apps” could be developed, as anything designed for the platform probably needs to be fully offline most of the time.