Version 2.5.1 for Mac and Windows
10 British Pounds, shareware
With version 4.mumble of iTunes, Apple no longer
supports copying songs from a person's iPod to
their hard disk.
They're obviously scared of
going anywhere near the DMCA.
This is annoying for many reasons, mostly ethically (the DMCA is a terrible law and should be tested and fought, not anticipated), but also practically. There are good reasons why one might want to move one's data from an iPod to another device. For example, mere mortals can't replace the batteries on iPods; instead, the whole gadget has to be sent in. So, either you have 20 spare Gigs somewhere (more than the size of my entire hard drive when I first acquired the iPod), or you make a backup of your data before sending it out, or move it to a new iPod as a whole. Except you can't.
Or, say, you start out using an iPod on a Windows machine and then make that "switch" to a Mac they're trying so hard to get people to do. Well, the Mac version of iTunes uses a slightly different filing system for its data, and, while it can play the Windows data, it can't convert from the Windows version to the Mac version. All it can do is reformat the entire iPod and then put a new version on it.
So, you can't get your old stuff out, and you can't upgrade your iPod. Every time iTunes loads, it offers you to "upgrade" the software on the iPod, where "upgrade" means that it will delete all your music.
That's an annoying trap, but one can live with it (and those offers of upgrades can be turned off).
Things got worse for me the first time I actually bought music via the "iTunes" online store. They don't tell you this before you pay, but the protection claptrap around the songs is incompatible with the old iPod versions. The music can't be moved onto the iPod unless the iPod is upgraded, and that, of course, deletes all your music.
I wrote a nasty letter to Apple (where, I'm sure, it is ignored with great style even as we speak), and googled for workarounds.
Podutil is one of the tools you could use to do what Apple says you can't and refuses to keep doing for free. You run it, it either figures out correctly what iPod you have or you tell it, it scans the iPod, and then copies the music you own from one device you own to another device you own.
Once you have your music back, you can import it into the Library (on disk). The playlists and ratings will be lost, and there will be much useless duplication from one file on a disk to another file on the same disk, unless you turned that off.
If you fork over the money early (I think you need to pay for it, but of course, now that I have paid, I don't want to go back and test the unpaid state), you can tweak the copy to automatically add the copied files to iTunes and import the playlist into iTunes as well, with an optional prefix. There's a little format language for the filenames, even. The playlist import didn't quite work for me - the prefixed thing ended up being the name of my iPod, not the name of the playlist.
The thing that sucks most is that I can't seem to get my ratings back, but compared to the damage that would have been done otherwise, this is fairly mild.
I still keep thinking I should have stuck with Linux.