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jump lists are windows specific as you noted & probably outside the program's control. I think that when program A calls program B ( e.g. calibre plug -in calls sigil) the jump lists do not update.
So how about a simple command line option or preference setting to have sigil open to its last saved file if that still exists, , rather than to a new document ? It already "knows about" that file - it is number 1 on drop down "file" menu.
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