@dmapr,
Just to backtrack a little... Am I understanding this right? Are you saying that the only reason that the standard built-in fonts Gill Sans, Avenir, Kobo Nickel are currently problematic with italic/bold is because those font files have incorrect filenames deep within the zipped up fw upgrade files? And this is the problem that the Kobo Developers have so far refused to fix because 'everything's OK in kepubs'.
If I've understood you correctly, I'm utterly gob-smacked

This surely would be a <30sec fix for whoever is creating the fw zip files? Personally, I never use those 3 fonts but it must be affecting a lot of users.
Update: Well I've answered my own question, I couldn't resist testing it myself. I have a Glo which was still on fw 2.6.1a, so I took a copy of the Glo 2.6.1b zip file and renamed the font filenames inside KoboRoot.tar (inside KoboRoot.tgz) using 7-zip
4 x Avenir*.ttf to Avenir Next*.ttf
4 x GillSans*.ttf to Gill Sans*.ttf
4 x KoboNickel*.ttf to Kobo Nickel*.ttf
Then I sideloaded fw 2.6.1b in the normal way. The 3 problematic fonts do indeed seem 'cured'... and it was painless.
Thanks, dmapr