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If you only plan on using the Bluetooth, you can't go wrong with a 1945 or 2215. If you want the additional connectivity of WiFi, you may want to go with a 4150 which has both.
Feature for feature, you probably won't have much trouble finding equivalent programs on the Palm OS, so don't worry too much about it.
I've made the switch twice (Tungsten T to Pocket PC to Tungsten 3 to Pocket PC) and have learned my lesson ;-)
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