iTunes will get the confused about the auto-sync if the iPod battery goes dead. This will mess up playcount tracking.
Avoid if possible. Nothing is as annoying as coming home after a long trip and finding that your favorite plays from the trip are not synched back to iTunes!
The data is stored on the hard drive, not in the player's memory. So it won't be lost.
However, there was a bug where the play counts file would be cleared when the iPod booted up cold, as in it had not been turned on in two days and had gone into deep sleep. I think this has been fixed in 2.1, but I have not tested it.
by Otto on Oct 29 | 6:57 am
I have noticed that if I let my iPod go dead, it sometimes forgets the date. :(
kurly: This is a question relating to dynamic updating of SPL’s using the following criteria (as an example):
•Grouping Contains: .p/a.
•Grouping Contains: ...
As far as I know - this doesn´t happen on the 3rd generation iPods! They will remember everything - even when the battery was empty! ;-)