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“Free software”, as in “free as in speech”, means the freedom to run the program for any purpose. This means using my music software to play music in the format of my choice; it means owning my media in a format that doesn’t lock me in to using one company’s devices; it means knowing the program will still be useful if the original creator stops supporting it or changes it in harmful ways.

Avoiding the “Sorry, dad” scenario described in this article that describes, albeit from a different perspective, many of the reasons I’ve transitioned from a Mac geek to fairly anti-Apple (similar reasoning articulated very well by Mark Pilgrim) is a big reason savvy consumers of the future will (should!) consider open licensing an important criterion for purchase of any product.
Elgan says:

At least with Windows, you could reformat your PC and install Linux or any number of other PC-compatible operating systems. Can I reformat my iPod and install something else? Can I uninstall iTunes but keep using the iTunes store and my iPods? Apple strongly discourages all that, claiming that the iPod, the iPod software and iTunes are three components of the same product. But that’s what Microsoft said about Windows and IE.

Well, fortunately it’s not that bad; my Apple-manufactured iBook and iPod didn’t become useless to me when Apple’s software stopped being worthwhile, because although Apple discourages the practice, they hadn’t started actively trying to prevent users from installing the (free) software that would do what they wanted. Judging by the encrypted firmware that’s preventing Rockbox from being available for the second-generation nano, they’re starting now.

So yeah, the iPhone is sexy and tempting, but when I have the cash in hand for something like that I’m buying an OpenMoko phone instead. The iPhone would work great for a while, but just as I wanted my music player to play .ogg files and I wanted my operating system to give me greater control over the interface, I’d soon enough want my phone to do something it didn’t already do; and at this point I’m not interested in supporting manufacturers who restrict my freedom to do what I want with the devices I’ve purchased.

In my never-ending quest to free myself from the fetters of non-free software and to amuse myself by putting new operating systems on things I find in my house, I installed Rockbox on my iPod nano recently.

It was essentially pretty easy. The hardest part was actually figuring out the difference between Rockbox and iPod Linux. It turns out that Rockbox is a music player, like the original Apple firmware, and iPod Linux is a Linux that runs Linux programs. I toyed around with iPod Linux (played some Tetris!), but since my goal was to have a music player, I moved on.

First step: converting my MacPod (HFS+, which Linux hates) to a WinPod (FAT32, a more widely supported filesystem). Interestingly, Mac OS, Windows, and Linux all recognize the WinPod, while only Mac OS and some subset of Linuxes recognize the MacPod. To convert a MacPod to a WinPod, just plug it into a computer that’s running Windows (if you can find such a thing!); you’ll automatically be prompted to reformat. You lose all the data on the iPod when you do this, so back up first if it’s anything important. After that, it’s just a matter of following the instructions here.

So now my iPod dual-boots, just like my laptop — and just like my laptop, it will rarely if ever see the Apple OS boot up again. There’s nothing that Apple’s iPod software did that I preferred to Rockbox, and plenty of things Rockbox does that I like better. To name a few: it’s free as in speech; it plays .ogg files (the .ogg standard is also free as in speech!); it lets me choose to keep my existing filetree organization, or use its ID3-based database, or both; it lets me put (any kind of!) files on it and then retrieve them on any computer under the same name and format; it’s highly skinnable, so I can get it to look more attractive than the original Apple look; and it allows finer tuning of settings (for example, I can choose whether or not it stops playing when headphones are unplugged, set how long it waits before going to sleep, &c). Using it under Linux (or any OS) is simply a matter of mounting it as a drive and then copying files directly to its filetree, rather than using a specific piece of software. Without a doubt, Rockbox has increased my ability to use this piece of hardware the way I want to.