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You should go to www.limewire.com and downlaod limewire and manually download each song and it'll help you have the music in your i-pod. Yoy can also open i-tunes and connect your i-pod home of your i-pod and check the box that says manually manage songs but that will erase the music you have in the i-pod but will allow you to put the mp3 files on the i-pod.
I also have the same problem but now I think it's the type of I-Pod you use. Do you use the I-Pod 80 Gb video or the newer 160 Gb I-Pod with the cover flow etc. ? The documention of the HTD7001 says it's only support some I-Pods. I would know sure if I would have a type of Video I Pod wich is supported by the documentation
to "manually update ipod" if it is set to autosync then all tunes in the library which are registered as being on the pod will automatically update. each time you connect the pod the itunes sw will update the pod from the library.
when the pod is connected and auto sync is active if you delete a tune from the lib it will update the pod and delete the same tune.