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The ipod file system is off-limits to the user, so, as you say, it is necessary to “break into it” if one actually wants root access (for example to set up an internet filter for iPhone / iPod, or for many other reasons). However the part of the filesystem which holds music files, podcasts and the like, is accessible. In other terms no jailbreak is needed. Also there is no DRM on iTunes downloads and iOS devices since a few years. Things can be moved freely back and forth.
If you wish to do directly without third-party software, this is definitely possible, however one needs to modify the “hidden files” option and do a few things in windows, it’s no big deal but it’s much easier to have a todo list while going through it. If you search, you will find the detailed instructions. I don’t post because links get deleted.
Both the third-party software and the operating system folders method will show the user whatever’s available. On a jailbroken iDevice it is all of the filesystem, which becomes completely accessible. On a non jailbroken iDevice it will be only those parts of the filesystem that iOS makes it available to the user to access directly.