iPod Shuffle issues, need some help

Recently I have been having some problems with my 2nd generation iPod shuffle. I've only had one of these, so I don't know if this behavior is atypical or not. Recently whenever I plug the shuffle in to load some songs on it from iTunes I keep getting constant "waiting for iPod" messages from my iMac. The orange shuffle icon on my desktop keeps flickering on and off (like every 5 seconds). Additionally, songs load on incredibly slow (my 1st gen shuffle and video iPod loads songs much faster) and during workouts I've noticed that songs have the tendency to "skip" a lot. Do you think something is failing on the shuffle and I should bring it in to local Apple Store for repair? Also I've tried multiple "restores" of the iPod in iTunes and it's plugged into a USB 2 opening, not 1.1. Thanks for your advice!