Personal: DOS -> Win3.1/95 -> BeOS -> WinXP -> MacOS -> Win10 -> Ubuntu -> Debian
There was definitely some dual booting in there, particularly in the BeOS (to Windows for Games) and Win10 (to Ubuntu for work) eras.
Professional: Debian -> RHEL -> WinXP -> Win7 -> Ubuntu -> gLinux/ChromeOS -> Ubuntu -> MacOS -> Ubuntu -> MacOS/Ubuntu




Sorry, I see that I was unclear.
Yes it fucking does require sending the data somewhere, specifically to every “application store”, which by their definition includes such things as Github, PyPI, Crates.io, Debian mirrors, apt/rpm repos, and personal websites that have hobby projects from more than one person.