Well if it doesn't support it well, then it won't pass the WAF(Wife Acceptance Factor).
Convert the wife's PC to Linux, and then load vmware or qemu to run the few remaining Windows apps that she's hooked on.
I'm not sure how well vmware will handle connecting to an ipod. I had trouble accessing USB devices directly from Windows within a vmware sandbox. Something about Linux drivers grabbing the device as soon as I pluged it in.
Alan
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