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I embed fonts using Calibre, and it really isn't that big of a deal. Under preferences, conversions/common options I set the default to embed the fonts I want and to "subset all embedded fonts". That keeps the converted file sizes smaller by only embedding the characters used in the AZW3 file rather than all the font characters. I also set the "Filter Style Information" tab to remove all fonts and margins--that way if the document already contains a font it'll remove it and replace with the font of my choice. I purchase almost all of my books in ePub format and then convert them to AZW3 for my PW2, so embedding the font during conversion is trivial for me.
Someday, I may be brave enough to try jailbreaking--it would be nice to add my own fonts directly to the Kindle and be able to switch between my fonts instead of having only one font per book.
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