Even though the copyright holder had specifically designated the files as freely copyable and redistributable for personal use, iTunes limits the number of times files may be copied from one device to another, or from a library to a device.
I ended up using a program called Floola to copy the files from my buddy's Mac Mini(not directly from his iPod) to my wife's Nano. Floola is multi-platform and can run directly from an iPod, so I copied the Windows(a standalone executable FLOOLA.EXE) and the Mac(a DMG file) versions to the Nano.
- Installed iTunes 7.4.3 from http://oldversion.com to my wife's PC and copied an album in MP3 format I had previously purchased from allofmp3.com to the iPod Nano using iTunes.
- Copied Mac & Windows versions of Floola to the iPod Nano & tested adding/deleting tracks - worked fine.
- Uninstalled iTunes from wife's PC.
- Went to Buddy's house, plugged in wife's iPod Nano and launched OS X version of Floola directly from the Nano.
- Used Floola to copy files from buddy's Mac Mini hard drive to wife's iPod Nano.
- Closed Floola, Disconnected Nano from buddy's Mac Mini.
- Verified that the files now existed on wife's iPod Nano.
- Returned home.
- Installed Media Monkey on Wife's PC as a replacement for iTunes, showed my wife how to use it in 20 minutes.
While the iTunes interface seems simple to use I really don't see the point in forcing Apple licensing limitations to media I already have the right to use. In my mind iTunes is crippleware because it restricts the playback, management, and transfer of media I already have the right to use and redistribute.
Additional Cons/gripes against the iPod Nano:
- $187 for only 8GB of capacity seems too expensive - that's less than 2 DVD-Rs of storage.
- The included USB sync cable is very thin - since the cable is used for charging(power) as well as data transfer and lacks additional shielding the transfer rate is likely compromised.
- Is my sweetie really gonna watch video on this tiny screen? Rarely, if ever. A monochrome screen with 32GB of storage capacity would be much preferred, allowing for storage of many more audio files.
- Having to pay $30 to install an after market protective cover(InvisibleShield) because the device so easily gets scratched.
- Small & light, bright display with good contrast.
- The wheel on the Nano provides a smooth interface. I wonder how often it'll get used by my wife since she's using playlists, though. It's a simple matter to find a playlist on any media player and hit play.