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I have both platforms and use both... but for different purposes. I have a Tungsten T3 (migrating to a TX) as well as a Dell Axim x50V. Both platforms have their strengths and weaknesses and both can do 80% the same stuff pretty well.
Basically, if PIM applications are most important to you (as it sounds they may be), you will probabaly be happier with a Palm because they are designed to handle that kind of app very efficiently. This does *not* mean that PocketPC's can't do PIM well, it just means that Palm devices are more efficient at this kind of app.
On the other hand, if you need (or like) VGA screens, and the optimum in multimedia or wireless, you'll likely be happier with a PocketPC because those devices generally handle those apps more effectively. That does *not* mean that Palms can't handle movies, MP3's, WiFi, etc. because they certainly can. It just means that generally, PocketPCs provide a higher level of hardware implementation for these apps.
Both systems suck at battery life (color screens and internal radio transmitters saw to that!) compared to the older B&W screen devices.
Both systems have their share of reported hardware or OS problems and have fixes to various degrees of effectiveness.
Also, don't worry about PalmOS going away in anywhere close to the forseeable future. The addition of Windows and Linux operating systems to 'Palm' machines will supplement, not supplant, PalmOS systems (or maybe Linux systems that act like PalmOS devices). The company is not about to abandon the roughly 20,000-30,000 legacy PalmOS apps.
If you select a PocketPC of some kind, you will just have to live with the fact that the various Windows OS's require more 'attention' (ongoing soft resets, etc.) than does the PalmOS. The former is just way more complicated than the latter.
Good luck.
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