On Windows, in a normal Python installation python.exe and pip.exe are not in the same location.
python.exe is directly in [PythonInstallDir]\.
pip.exe is in a subfolder [PythonInstallDir]\Scripts\.
This seems to be the root cause of the problem.
In a venv, python.exe and pip.exe are both in the same location, [.venv]\Scripts\.
Would it not eliminate or at least reduce the problem almost completely if that was the case also for the normal Python installation?
Preferably, the Scripts subdirectory would be eliminated and all executables would live in the toplevel install / venv directory.
If backward compatibility is an issue, duplicating them in both locations could maybe work.