Doesn’t wine expose your system disk as disk Z to programs? Any info stealer can potentially find your .mozilla or .chromium directory and upload it to some server.

The point is, none of this is a security layer. The risk is probably low, but it should be properly understood and mitigated - which OP is trying to do.

You don’t need VMs for this, it’s literally the original game.

How can you validate that if you don’t have the original game to calculate and compare hashes?

Do you actually keep sensitive data on your self hosted systems?

People self-host photos, documents, code, passwords, chats, and other sensitive stuff. Even Jellyfin in your example can get you into legal troubles if your pirated (or even legally obtained and ripped) content suddenly becomes public.

What am I missing?

That it’s 2026 and our lives are heavily digitalized. I’d understand this question in 2000 where you’d probably host a few html files and a counter-strike server, but come on.