FWIW, here's what I've experienced. (I'm currently using Sigil 0.9.9, built from source, on Kubuntu 16.04, but it's been like this since "forever".)
To select multiple consecutive chapters in the book browser, I click on the first one, then shift-click on the last one. For a moment, all are highlited, but the highlight disappears for all but the last one. If I shift-click again on the last one, all the highlighting re-appears, and stays.
I don't seem to be able to ctrl-click multiple files at all, consecutive or otherwise.
Albert
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