If IPod Shuffle won't connect, try cleaning headphone jack
I was having this issue where my good old iPod Shuffle (4th? gen) wasn't connecting to any computer or power source. I cleaned the headphone jack by putting rubbing alcohol on a cotton ball, rubbing a 3.5 mm plug with it, then inserting and reinserting several times. I guess that cleaned some gunk off of the contacts...Now connecting/syncing better than before, maybe good for another decade or so. Hope this helps somebody out there...
iPod shuffle