Hi, The Itunes software can be set to convert the downloaded unprotected files to the MP3 format. You don't need Itunes to download MP3 music and you don't need special softwar to copy (syncronize) the files to the portable device. Windows recognizes a portable device, connected via the USB port, as another drive letter. You can then use the Windows (or command line) copy command to transfer files to the drive. I'm not yet a full Linux user but I suspect it can transfer files to a device attached to the USB port. The MP3 player has a folder structure so you can choose to manually put the files where you want. Personally I have ripped music files from CDs and copied them from vinal records. These are manually copied to the Olympus DS50 digital recorder. It plays MP3 and WMA files. The folder structure is limited but I don't need the many layers of Categorizing. I hope that this helps.