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epub and kepub are two formats for ebooks. They are, essentially, the same. The difference is that kepubs are specifically from Kobo (though you can convert epub files to kepub files using calibre and certain plugins). Kepubs have some special features in regards to record keeping and reading statistics.
You can have otf fonts and ttf fonts on your Kobo, however as noted ttf fonts are generally a better option because they work with all aspects of the Kobo. The font file should end with either .otf or .ttf for the respective formats. Font Forge can be used to convert from one to the other. You don't really need to worry about knowing more unless it's something that interests you. It's not something which particularly interests me, or I'd give you more information.
I don't recall off hand, but I think bookerly comes in .ttf, so unless you converted it or the source you got it from converted it, this shouldn't be an issue. However Bookerly has had some odd issues on Kobos, mostly oddities in improperly using or not using the bold variant.
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