Technology

Ah, you're looking for quite specifically the workflow in Windows. That isn't quite as commonly possible and yeah, I don't think, Xfce can do it. If I remember correctly, it had separate shortcuts which you could bind specifically for the diagonal tilings. But your analysis that it needs conditional logic is correct and Xfce in general tends to err on the side of simplicity there (usually allowing for greater modularity and customizability within those simpler bounds).

Personally, I'm on KDE and I think, it essentially works the same as on Windows.
One difference is that Super+Up/Down actually tiles the window to the top half and bottom half of the screen. But if you press Super+Left and then quickly Super+Up, then it will end up in the top-left corner.

I imagine, the Cinnamon DE would also replicate this behavior, possibly even more faithful to Windows. That's kind of their thing, that they mimic the workflow from Windows closely.

For the middle-mouse scrolling, Firefox has an option to turn that on, called "Use autoscrolling".
Other than that, though, yeah, I'm not aware of that being generally available on any DE. KDE has nothing.

The middle-mouse button is traditionally used on Linux to paste from a separate clipboard which is filled whenever you select text. Kind of a weird workflow artifact, too, but lots of folks have muscle memory for that, so it stays around...