I still think the best option is a command line flag like "--open-in-homedir" that causes Idle to do a chdir to the user's documents folder. This way we can put a static option in the start menu item in the installer and not worry about the limitations of MSI, etc. These limitations also exist in MSIX (app store packages) which is coming soon as well.

Alternatively, we could check the current directory to see if it matches sys.prefix (or whatever it matches) and chdir in that case. No option needed.

For reference, VS Code requires "code.exe ." to start in the current directory, and otherwise uses its default no matter where you start it from.