FWIW, I tested with with stock Sigil 0.9.9 on Mac OS X, I can NOT recreate any of this.
I can click on a chapter in the BookBrowser and then shift click a bunch of contiguous files and it highlights just fine and I can drag and drop them to a new location with no problems.
I can also click on a file and then Command click (apple key) on another file (not contiguous) and happily drag and drop those as well.
So whatever issue this is, does not exist on a Mac so that kind of points to a Qt issue of some sort.
That said, there are many programs that look and and remap keys (control and otherwise) that could be interfering including a user's own key settings in Sigil's Preferences.
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