Replying here in case someone comes along this question down the road like 
I did.

As far as I can tell, the reason Mezzanine's FileField doesn't behave like 
Django's models.ImageField or models.FileField with the UPLOAD_TO_HANDLERS 
is that it's using the 3rd-party "filebrowser_safe" file-system manager.

This is what allows it to present the popup GUI of the file-system. In 
order to get functionality similar to models.ImageField or 
models.FileField, we'd have to modify Mezzanine and/or filebrowser_safe, 
which, as noted above, removes your ability to update.

It's frustrating that we have to choose between a dynamic file path and a 
user-friendly GUI, but I understand why it's there.

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