The time requirement is troubling because each device has to take the entire time to sync any changes--aka, time to convert each full song times the number of devices I sync.
Thats the problem, the curent system is the simplest you could have with just a device or two. Need to sync a portable -- do a conversion on the fly and you're done.
I'm not sure if keeping several versions makes things any easier. Assuming diskspace is not an issue, what will you sync procedure be like ?
Ahh, device a, so select library of low and sync.
next device is high, so again select another library etc
How do you keep tags in sync between all these copies, assuming you use rating as a criteria to select music ?
The only option i found was to go mp3 and be done with it. If you use good encoding options the differences between lossy & lossless are minimal.