@Colonel Cathcart,
The Bookerly bold/italic issue is a known problem when using Bookerly on a Kobo. It is fixable if you want to take the time and trouble. The solution is
documented in the Kobo Wiki. The example used there is Amazon Ember but the technique can be used on any font which displays the same symptoms.
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btw, I also noticed the difference in ligatures (or lack there of) between the two screenshots (very clever choice of word, office, well done!) and since turned on optimizelegibility in the Kobo config file. Now I'd also like to turn on Kerning, if possible, for kepubs.
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The optimizelegibility setting should enable both ligatures and kerning in kepubs. This does, of course, assume that the font you're using contains both those features.