I think I just found out the real issue, and that information is not
going to help you because it will contain seemingly random indicators
depending on how I size my windows.

VMware Player, like most virtualization software, runs windowed by
default, and that window is dynamically resizeable. Now someone in all
their wisdom at Ubuntu apparently decided that the available scaling
options depend on the current resolution.

So when I keep the settings screen open, and start resizing the window,
thus dynamically resizing the "monitor", I can see the available scaling
options change in real time. At 3840x2075 (that's 4k minus the VMware
window borders) I see the 100/125/175/175/250 selector, at 3480x1859 I
don't even get any fractional scaling options, at really low resolutions
all scaling options disappear.

When VMware Player boots, it snaps to the default 1024x768 size. So
that's the monitor resolution when the desktop loads, it concludes
scaling is not allowed at that level, and resets to 100%, no matter what
it was before the reboot.

The real issue appears to be: scaling settings should not be modified
based on resolution during boot.

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https://bugs.launchpad.net/bugs/1884754

Title:
  Fractional scaling not persisted in VMware Player

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