Yet More Update:
For whatever reason, the azw3 file from Amazon I got for theduck's originally reported book did not mark its font file as encrypted. In fact, the entire file downloaded unencumbered by DRM.
A couple azw3s that I downloaded do contain 'encrypted' font files.
Looking at the calibre code, there is an 'encrypted' flag in azw3 for font files, although I don't see any actual decrypting happening.
So apparently Calibre is just honoring that flag on conversion and encrypting the fonts on output.
I don't know why my constructed azw3 with a "100% free" font still comes through flagged encrypted.
All of this is just documenting my research as I try to decide whether I want my epub plugins to decrypt(/re-encrypt) font files or declare it the users' problem.
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