I haven't worked with an IPOD, but Debian (and Debian derivatives such as Ubuntu) Linux offers several tools for communicating and working with the ipod without going through itunes. It also has a fair selection of "rippers". It's been awhile since I ripped any, so none loaded at the moment to tell you a name of a good one. Cool thing is, it's all free, the Linux OS and the rippers and communications protocols.
If you have a spare computer or even a spare Harddrive/partition, you might try downloading a version of either Debian or Ubuntu (I prefer Xubuntu, put that is personal preference) and work with it for awhile.
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