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The only thing that worked for me was Kyl's tip.
I named the files as Bookerly.ttf (Regular), Bookerlyb.ttf (Bold), Bookerlyi.ttf (Italic) and Bookerlyz.ttf (BoldItalic). The same trick worked with Amazon Ember which was showing the Bold style for Regular until I used the same naming scheme.
Note that you need to reboot the Kobo after renaming if you were using the font previously or at least switch to a previously unused font size, because the Kobo caches the generated pages.
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