Well I'm all set now.. not sure if it's related but once I finally got things working Apple was asking for reconfirmation on my payment info since I was accessing it on a new iPad and new install of iTunes on two computers.
After updating iTunes yesterday, I noticed that several of my playlists are broken. They HAD music yesterday, today they show none. Not across the board, which is what is confusing, but several playlists are empty now.
This is on a MacBook Pro, not the device listed in signature.