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Not just Windows, but Macs as well; I’ve had three different generations of MacBooks that you could plug a USB-C (thunderbolt) into any dock (Dell, HengeDock, random amazon brand, etc) and they simply worked.
I do feel your pain about multiple monitors; it is even more evident when you try to run some of them rotated and/or flipped.
I’ve not found a solution for it yet, and in some small way, I am glad to hear it’s not just me having these problems.
And that is not a good thing.