Crossfade on Mac
I'm not sure what the issue is - I have the most recent version of iTunes and my playlists are synched on my computer. The crossfade option is available in preferences but my music isn't crossfading. Am I missing something?
Safe Boot from the HD, (holding Shift key down at bootup), does the problem occur in Safe Mode?
Safe mode attempts to repair Disks & clears lots of caches, so if Safe Mode works try again in regular boot.
To find out if it's system wide or user specific, try this...
Open System Preferences>Users & Groups, unlock the lock, click on the little plus icon, make a new admin account, log out & into the new account.
Does it work in the new account?