AZ-J
Riding where it's hot!
660 came with 2.8. No issues with the Mac Web updater. In fact, I haven't had any issues with it for a long time.
If it says 2.80 on main screen after Software Version, you are good. But if it says 2.70 there and 2.80 after GPS in sub-screen, it needs an update,
So, assuming your 660 came with Software Version 2.80, you got the latest version of the 660 and you are good. Still, your version of Mac Webupdater is known to look like it works but after a 660 check, yet it does not communicate with the 660 correctly, just as the new PC version mostly works now, as well. Both say they have correctly updated the voices and such but sometimes does, and sometimes does not, after the 660 is checked.