iTunes permissions on second drive
Here's the deal w/ iTunes in regards to moving your Users directory to a separate drive or partition; it turns out that the Shared directory must remain on the system drive. For example, in my context the path should be /Mac/Users/Shared where 'Mac' is my system drive. The other users stay in /Volumes/Pig/Users/..., i.e., arrow and wildcat.

I believe the permissions I listed above are incorrect and they've since been changed to:

/Volumes/Pig - 644 system:admin

/Volumes/Pig/Users - 644 system:admin

/Mac/Users/Shared - 777 arrow:admin

Correcting the permissions to their current settings didn't solve the problem on it's own, moving Shared to the same drive as the iTunes binary did.