Out of curiosity, what software? It won’t run with Wine? Maybe there’s a decent enough alternative?

You don’t even need to “pirate” Windows anymore. You can download an ISO from Microsoft’s website, install it, and when it asks for your license key, you click “I don’t have one”, and that’s the end of it. If you look in the activation settings, it’ll say “not activated”, but nothing will ever become of it. This even works if you install it as Pro. It’s not like the Windows XP/7 days where you’d get a 60 day scare timer. They just don’t seem to care anymore, or maybe all that telemetry they siphon up from you is just that much more valuable.