Multitasking really is more of an academic issue than a practical concern for me, since I only really care about SSH and playing music. All the rest is negotiable.

My showstopper would have been hardware compatibility. My choices for (locally purchased) Palm-supported hardware were limited enough as it was. If I'd held out for a Linux handheld, I'd be spending all my time hunting and hacking instead of just using.

And I don't wanna hear you complain about a $47 keyboard. :) You're living in the land of cheap electronics. The only keyboard I could find that was worth buying cost over $100. (But at least it's better than some laptop keyboards I've met in my day.)