I know you can't put data INTO your iPod on the road, but if all you use a PDA for is info retrieval from stuff you've already entered into iCal or Palm Desktop, then might it suffice? (i know that is ...
Backward compatibility; there are lots of third-party applications and conduits that use the Memo DB. I can easily think of a kluge around this, and it seems to me that OS 5 would have been a fine ...