Been doing that for the past 15 years or so, being able to use group policy is essential with Windows. I'm pretty sure my son really wants to upgrade his last computer (to Linux), but I may have more work to convince the wife.
I always just bought grey market keys (for Pro/Enterprise), in nearly 20 years I never had one fail or quit working randomly.
Because she still like the familiarity of Windows. She doesn't do anything specific to Windows, just doesn't want to leave it yet.