Is it even piracy when Windows allows you to use it unactivated?
It’s nagware, like WinRAR.
Oh, you mean the never ending forty days.
Technically yes.
MassGrave exists these days but almost all laptops come with a Win10/11 license anyway now, probably enough legal grey area to CYA for personal use but I wouldn’t risk it for anything for-profit, even a startup.
Until recently he's run his corporate infrastructure on Windows servers. Not quite the same league as reinstalling on hardware with an existing license.