Syncing large library & playlists with 4GB ipod

I have a 4GB ipod that I manually manage because my iTunes library is too big. I haven't synced since January (when I got a new ipod). I used to be able to drag on-the-go playlists to iTunes without problem and now I can't. Did they get rid of that capability in the new iTunes releases? I can't do auto-sync due to size. Is there no other way to get on-the-go lists back to iTunes when I HAVE to manually manage.

ptoland wrote:
is it normal to have challenges based on the configuration I've described?
well, my library weighs in @ 1.5 TB. i have two identical firewire 800 drives (one main, one backup) hanging off my mini. when i initially cloned HD no. 1 to HD no. 2 using CCC, it took in excess of 12 hours.
if you're syncing large amounts of data via your network (especially if you use wireless, which is not very reliable for such a job), yes, i would expect to expect such challenges.
have you tried if a wired connection improves things ?
any specific experience with the suggested software downloads?
personally, i use *home sharing* so, no, i don't have first hand experiences with those apps.
JGG

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Syncing large library & playlists with 4GB ipod

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