I've challenged you a couple of times already. You keep writing walls of text without proving anything you claim.
You've not proven that you can "easily" run old graphical software in your modern Linux.
You've not proven that Windows is leaking data left and right.
https://news.ycombinator.com/item?id=42557373
Knowing that Microsoft uploads WiFi passwords to its servers does not even need wireshark. You just need to log into the same Microsoft account on a different machine and observe that your WiFi passwords are synced. Given that the upload is likely encrypted, it would be difficult to observe the passwords being uploaded to Microsoft servers using wireshark. While you would see the packets, you would not know what they contain unless you somehow get the encryption keys out of the system encryption library.
Your prior remarks on running old Linux software did not require that things be easy, which is a matter of opinion, or graphical. It is possible with the right libraries as modern Linux systems (minus Android unless you install a X11 server) can display X11 applications.