Phc7006: What can I say ? I trusted MS regarding DOS 2.0, 3.1, 5.0 and 6.2, then regarding Windows 3.11, 95 and 98. Then that trust was damaged by Millenium, restored by XP, redamaged by the tactics used to push Vista ( upgrades gradually ruining your install ), I stayed away from Vista, got 7 but with some distrust, just to go beyond the point of no return with the inclusion of telemetry and other darwinian nightmares. So ,yeah, dual boot 7 / Opensuse is what I'm using now ;-) , except on my "business"laptop ( read bought at my cost, but with specs allowing connection with corporate systems ) where I was forced into Win 10 a few months ago
With the exception of DOS 2.0-3.1, virtually everything you said mirrors my experience pretty much exactly. I stuck with XP primarily because it did everything I needed just fine and any quirks it had were manageable in the latter years of its support. I didn't find it materially lacking in features or other aspects for my needs, so I decided that I had no reason to upgrade it to something newer - until I had a reason to, plus because my computer was older and the newer OSs had higher system requirements I would either have to upgrade the hardware I had or expect a terrible degradation in performance that would make the system unusable. It already was struggling to run games and certain other software so upgrading just the OS was not an option, but continuing to use XP worked fine for most things, just not games and a couple other apps, which were ultra-slow. But upgrading was a non-starter too as the system was so old that "upgrade" basically meant "remove DVD writer, throw PC in the basement, build entirely new PC and install DVD writer" which I had no compelling reason to do - until I had a compelling reason to do it. :)
The compelling reason to finally upgrade ended up being a hardware reason - my GPU died, along with a RAM stick which meant seriously degraded performance that was becoming increasingly unusable. I knew I had to start planning to build a new system or I'd end up downgrading to other even older and even less capable hardware I have, which was a non-starter. Plus, it was early 2013 and I knew XP only had one more year of official life left in it so I knew I'd have to change my OS within a year anyway and the most viable thing at the time was Windows 7. So I built the new PC and a buddy gave me one of his Windows 7 license keys which sunk the deal. Overall the hardware and OS change went remarkably well I must say and I felt and still feel that "Windows 7 is the new Windows XP" so to speak.
But now I feel as you say WRT to the telemetry but I think you might have meant Orwellian nightmares. :) I run about 6-8 Linux virtual machines on this desktop mostly running CentOS 6 and 7, 2 of which are developmental desktop VMs for application development and web development. While I have other Linux desktop VMs I use for certain compartmentalized usage contexts, I plan on increasing the number of them over time and also eventually building a new dedicated Linux desktop PC however that's low priority for now, but as 2020 nears it will become increasingly more important to me for sure. :)
I wont be forced to use Windows 10 on my desktops or other machines, however I will probably end up forced to have at least one Windows 10 virtual machine at some point as a business necessity for compatibility testing of website development as I'll need to ensure things work on Firefox/Chrome/IE/Edge on all supported OSs, so I may end up needing that - but it will be severely isolated if and when that time comes, and wont be used for anything _but_ web testing and most likely firewalled off the Internet completely. Even then only kicking and screaming. :)