Looking at the table below, is this expected, or is it a bug?
it's debatable. From the plain algorithm, your expectation is right and the result is buggy. But one can argue that the actual result may be less confusing to the user (ellipsizing is clearer when the 3 dots are encosed by words. I've never seen a ellipsizing that cuts of the entire front).

Also, your code doesn't seem to support Windows path separators
What do you mean? I used G_DIR_SEPARATOR everywhere. I didn't test on Windows but it should work.

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