>How do you manage multiple monitors with MacOS? I was doing this until recently and every single login involved rearranging my windows because MacOS moves them all to whatever display woke up first.

At least for apps that are dedicated to one screen + virtual desktop, right click its icon in the dock and assign it to that display and workspace.

Note that the effectiveness of window restoration also depends on the make/model of your monitors – many manufacturers incorrectly share EDID's across all units of the same model and sometimes across multiple models, making it much more difficult for operating systems to uniquely identify them.