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I recently discovered there's an issue with the combination of macOS Catalina, Illustrator (at least) and 4K.
I will follow up with specs.
—Same behavior with current Illustrator 2020 (24.2.1).
I just changed my color profile in the preferences from my calibration profile to Apple RGB and that did the trick!
Adding to the list in the initial post.
Still, searching for a solution since I need to work on a calibrated view.