Can one keyboard shortcut open PIP windows for several virtual screens?

Yes. Use explicit display selectors in separate CLI commands, then run them together from a macOS shortcut. This avoids moving the pointer between virtual desktops to choose which display a keyboard action affects.

With BetterDisplay running, both virtual screens connected, Pro enabled and Screen Recording permission granted, these commands open each screen’s default PIP window:

betterdisplaycli set -name="Virtual Left" -pip=on
betterdisplaycli set -name="Virtual Right" -pip=on

Replace the example names with distinct names from your setup. Use -pip=off to close the windows. If you want a different saved PIP configuration for a display, add its identifier, such as -specifier=2. Create that configuration in BetterDisplay first. If you omit the identifier, the command selects configuration 1.

In macOS Shortcuts, add a Run Shell Script action containing both commands and assign the shortcut a keyboard shortcut. Use the actual absolute path to your installed betterdisplaycli executable in that action, since Shortcuts may not use your Terminal shell’s search path. Check each command’s result and confirm that both windows appear.

This starts the selected PIPs explicitly. It does not diagnose a separate Start Automatically failure after an associated display reconnects. See CLI PIP examples and Shortcuts with the CLI for setup and more window options.