Problem putting songs on shuffle from network drive

Hi - I was hoping someone here might have an idea on a frustrating problem I've been dealing with since I purchased a Network Attached Storage Drive.
Prior to having the drive, I had my music on my laptop and it x-ferred to the 2G Shuffle no problem at all. Once I've moved my music to the Network drive, synching is next to impossible. If I select a playlist w/about 200 songs or so, it will not transfer. I let it run overnight and it was not finished after over 8 hours. Itunes keeps saying updating ipod, do not disconnect. If I cancel it, I'll have about 15 songs on the ipod and the remainder did not transfer.
If I do one or two songs at a time, I have a 50/50 chance of it working one or two songs at a time, it won't change from the updating songs do not disconnect message if it doesn't work.
Does anyone have any ideas? The song bit rates are anywhere from 128 to 320, but has no bearing on what will end up working and what will not. Thanks in advance

well, i just do it the way i always do. I check all the songs I want updated (which includes the ones that dont work) and hit the update all button. All songs will show up except the ones i got off my website. No message will appear saying it did'nt work or anything. I tried just adding the songs that dont work and still they dont show up in my ipod.

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That's a shame.
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