Converting Video for Use on iPod Nano

I wanted to leave my kids some video messages on their iPods for camp (7th generation Nano devices). I did this last year using the Photobooth app on the Mac and just loaded them into iTunes and there was no problem. Naturally this did not work again. Linux to the rescue, however.

Syncing an iPod Nano with Windows under VirtualBox in Ubuntu

I bought an iPod Nano (7th generation) for my son, and decided I wanted to use a Windows 7 virtual machine to house the iTunes software necessary to manage the gizmo. Apple items need to be managed with iTunes running on a Windows or Apple computer (there are options for dealing with iProducts from Linux, but since this is my son's gizmo I don't want to have to deal with them). I have been using Linux on my desktop and laptop for some time now, and the only things I use that have to run on Windows (for which I created the VM) are some tax software and the sync software for the Fitbit. And now this.

Since tax season is past and since my Fitbit split apart into a kazillion pieces, I have had little need to run the VM, so the first problem I had to deal with was the excessive number of Windows updates to be sifted through. Once that was done, installing iTunes was easy but connecting to the iPod was unsuccessful. Windows kept telling me that it could not start the device, could not find the device, could not find the appropriate driver, etc. It turns out that the problem was USB 2.0 compatibility--the iPod quietly requires USB2.0 and the current version of VirtualBox doesn't support it directly. Instead of going through the whole troubleshooting story, which would bore you to tears, I will just cut to the chase and tell you the things I did to get it running properly.