As far as Ubuntu running in a linux/windows environment, that is no problem. You would run SAMBA which allows the linux to share its disks on the network so Windows can see it. You can move files to/from windows, update files on the linux side, modify with mp3tag from the windows machine. That's what I have running. There was a learning curve, and was some work getting the Samba service setup the way I wanted. You might look into the Vortexbox application - I believe there is a complete Vortexbox "appliance" available which is integrated hardware and software, but I think you can also get just the software which is a Linux OS setup with Squeezebox Server, SAMBA, and also apps to rip CDs directly.
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