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.
I don’t know, I remember them being great from a HW point of view (I had an iPAQ 514 and it was mindblowing even without touch and just a tiny screen), but UX wise…
I now have another iPAQ with a stylus and touchscreen, and I’m grateful back then I did not have it nor the mobile version of Age of Empires… it’s addictive stuff and a crazy good port. I don’t remember anything so good on PalmOS 5 (we had a Garmin iQue 3600, with integrated GPS and navigation… also very futuristic).