Is it safe to say that the "Update Automatically" option will update when the 2.3 beta is released late Feb/early March? Or is that a new version altogether?
Simplifying it a bit:
current 2.3 beta gets packaged with installer and released as MusicBee 2.3
If you aren't already using the 2.3 beta (although Steven has suggested you do, to take advantage of the improved tagging algorithm)
then when you start MB, you will get a message that a new version of MusicBee is available.
Steven usually then takes a (well deserved) break before starting on the next beta version.
Hope that clears it up for you, HossStyle