The issue looks like an upstream one, could you report it as well on 
https://gitlab.gnome.org/GNOME/gnome-shell/issues/ ?
The fact that the screen is forced back to its non-rotated mode when connecting 
the other display seems like it could be the same bug (shell refuses to handle 
rotations when an external screen is connected)

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https://bugs.launchpad.net/bugs/1807539

Title:
  Screen orientation is locked if external monitor is connected

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