It took forever to boot. When I dropped mine and broke its disk I then swapped in a 6GB disk and it took even longer, around 2 minutes. I went back to an mp3 discman instead before getting a Mac mini in 2005, which opened my eyes to the fact that Apple made more than just pretty devices, they cared about UI and paid attention to details like having different volume settings for headphones. I then bought a 60gb iPod w/ video and haven't looked back.
The Nomad Jukebox was great for the tactile-feedback buttons and it's durability. It was a tank.