I had tried several times to connect to my iPod, but it displayed the "connecting" screen indefinitely.

I use an alternative to iTunes called ephPod. I'm pretty sure that the last time I used ephPod, I disconnected my iPod w/o using the "disconnect" option - I just removed it. I'm guessing that this put the iPod file index into a weird state.

This morning, I hooked my iPod up to iTunes and did a proper "eject iPod". Now my Chumby can "find" it quickly.

Hope this helps someone!