SystemUI uses the following to determine if freeform multi-window mode is available:
java
mHasFreeformWorkspaceSupport =
mPm.hasSystemFeature(PackageManager.FEATURE_FREEFORM_WINDOW_MANAGEMENT) ||
Settings.Global.getInt(context.getContentResolver(),
DEVELOPMENT_ENABLE_FREEFORM_WINDOWS_SUPPORT, 0) != 0;
DEVELOPMENT_ENABLE_FREEFORM_WINDOWS_SUPPORT is hidden, so you would need to replace that with "enable_freeform_support":
java
boolean hasFreeFormWorkspaceSupport =
getPackageManager().hasSystemFeature(PackageManager.FEATURE_FREEFORM_WINDOW_MANAGEMENT) ||
Settings.Global.getInt(getContentResolver(), "enable_freeform_support", 0) != 0;
I don't have Android-on-Chrome-OS or DeX to test this on, however, this is how SystemUI is checking if freeform multi-window support is enabled. Perhaps you could decompile the settings or systemui app from DeX or Chrome and check if they have made changes here.