Files on the Jukebox could be easily updatable via wireless network. You would simply put an 802.11b or 802.11g adapter in the jukebox, and one in your laptop or desktop. Next, it would be easy to set up a share on your jukebox computer via windows file sharing, and simply map it as a network drive on the computer you are using to update it.
Additionally, you could load WinVNC on it, and be able to remote control the computer in the jukebox from another computer via wireless. Microsoft Terminal Services would also work for this.
When doing this, I would recommend implementing a password to secure your computer.