Next time you can't see the ipod in itunes, check the toolbar at the bottom of your screen. If the pc recognised the USB connection, you'll have a small icon that you can click on to safely disconnect your ipod before disconnecting the USB cable.

 

none of the accoessories that works for other ipod usually don't work for 5th gen video ipod. itrip won't work for sure.

 

it also happenned to me last time. I turned off my computer and the "do not disconnect" text on the ipod went away, then I disconnected it, and it worked normally since then.

 

My nano has been freezing up a lot on me lately. I usually can't just press play to turn it on, I have to hold the menu button for it to boot up. I never had any problem with my ipod mini, but the nano is a different story for me.

 

its probably going into an extended sleep mode. this is normal for ipods. if you don't use it for a day or so, you gotta hit menu to turn it on. that happens with mine too.