I am a diehard Mac user and have used the Handspring, Zire 71, Treo 650, and now have a Treo 700p. All have worked fine with my Mac, other than the common stuff that always happens.
During my Zire 71 stage, I finally bought a Verizon phone, and within a year decided I tired of carrying two devices with me. I used the Treo 650 until I lost it and upgraded to the 700p.
I use Missing Sync which seems to work better than the Palm Hotsync. As for categories, Palm's program will only handle 15 categories which has been a frustrating feature for me. Palm has a new CEO who worked on the iPhone, and he is revamping the Palm line including a totally new software program. His goal is to have it out later this year, and he is revamping the hardware design as well. I suspect it will more in the iPhone direction.
The Zire is the latest Palm Product I used without a phone. I am curious about the problems you described. I suspect you ended up with two of everything when you least expected it. That has happened to me, and once I realized why it happened, I know how to avoid it.
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