1. The changing cradle connector. The Palm V can't have the same connector as the other Palms, but often the changes seem to have been made without any engineering need. Imagine a household with 3 Palms and 3 distinct cradles. Right. This is ridiculous. See also #2. Oh, and why is it that only PocketPC devices have a cradle transformer that can double as a portable charger?
2. Neglect of the IR port. This relates to #1. My biggest doubts about Bluetooth arise from the incredibly neglect of the very reliable IR interface. If the cradle supported IR sync then the need for a single cradle interface would lessen.
3. Reliability. My wife's hack-free Palm IIIxe had recurrent "flashing logo" crashes -- total data loss. This happens once and the non-techie never trusts the device again. Since that time my wife uses it essentially in read-only mode and for game playing. My experience with this and the Vx (power switch design defect, non-reliable portable charger) has been that Palm reliability has degraded significantly since the Palm III. This seems to be a combination of hardware quality and OS fragility. An OS as simple as the Palms should not crash - ever.
4. Arbitrary limits: The stupid document size limit, the problems with categories (esp. if one edits both on the desktop and palm), the clipboard limit, the unworking undo function.
In short, fixable problems, but the neglect of each of them suggests a much deeper problem with Palm Inc. That's the real problem that we don't know how to fix.
PS. Re. 802.11b -- what about the power consumption issues? I thought 802.11b would simply suck a Palm dry.