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The filename issue (though maybe not the font not appearing on the Kobo device) is the same issue that I'm wrestling with -- when using Calibre to convert a Word DOCX to EPUB with embedded fonts, the resulting fonts will always have spaces in them (regardless of the names of the font used in Word). I'm not sure if this is Word or Calibre adding them, but it does create problems for at least many EPUB submission sites. To be fair, that doesn't mean it will necessarily create a problem when trying to send the EPUB directly to a device like the Kobo Clara or Libra.
Still, a lot of these hassles would go away if Calibre, like Word's PDF exporter, would just strip out the spaces in the embedded font file name. GhostScript, the open source PostScript converter (commonly used by third party PDF creators) also avoids adding spaces when it embeds the font. So far, Calibre is the only program I see that always adds spaces, but I can't rule out definitively that Word is doing it and then Calibre is just passing that problem through to the final EPUB, but I can say that all the other programs I've tested don't do this.
Note that if you're not embedding the font the Libra will use the closest matching font on the device. It's only if you embed the font that the filenames have a problem. Could this explain what appears to be an intermittent problem?
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