SirGrant, thanks for the answer.
I own an Ipod too (as you, I have bought it before I ever knew about free software). I think that we should also point out our attention on the operating system, not only on the software that could be used to handle the device.
For example, the Macbook is sold with a non-free operating system, but that operating system can be replaced (a part from BIOS that is a problem of most of the notebooks). So the notebook can work with a free operating system.
I think that, in the case of portable devices (if the software inside them is accessible), we should consider those device as computers that have to give the possibility to install (inside them) a free (even if simple) operating system. The fact that they can be managed by means of free software I'm afraid is not enough. Anyway, I don't know if Ipod has an accessible operating system or not.
Also, I'm not completely sure that the fact that the operating system of the device is accessible or not-accessible is the right way to distinguish
I think we could start a discussion about the operating systems that run on such portable devices and then create a list of the ones that are free software. Then we could allow users to insert devices only if they have tested those devices with one of the accepted operating systems. This is more or less what is done for the notebooks.
Perhaps there are better ways to operate. I don't know how it could be possible to distinguish (automatically, i.e. by the h-node users) between those devices that have a non-accessible operating system and the ones that have an accessible operating system. In the last case, I think, we should assure that the operating system is free.