When the behavior of modern software is virtually indistinguishable from that of malware and viruses I'll take my chances.
Upvoted as "Computing Quote of the Year"!
Besides all the other valid comments on this topic herein: I look at how I intend to use the tool, and weigh that against the advantages/disadvantages of whatever "upgrade" is being proposed. In my case, the tools I use run fine on Win7. I also know how to fine tune Win7 to do what I want - and not to do a lot of what I don't want (example: At rest, Task Manager reports a grand total of 41 processes on my workstations). I could give all that up for Win10/11 and gain... what? More intrusiveness, less control? How does that move my marker forward?
Oh yeah, Win10/11 "gives" you random resets and dead time too, often at the least convenient times. Literally as I've been typing this my wife, across the lab at her desk, just let out some choice words because her Win10 laptop just decided to "upgrade" again. Right when she needs to send some things to people.
Maybe Microsoft needs to ship two versions of their operating systems: The "For Dummies" version and the "Take your Chances" version. I'd gladly pay - extra - for the latter if it meant they'd leave MY optimizations alone and not open a bunch of outbound TCP sockets to somewhere.
I just want a tool. One that does what I need, in the manner I configure it, with no extra hands "helping me" changing settings and updating files. The fact that all of my systems run Win7 SP1 and I have yet to find anything that even slightly tempts me to move to anything later is a huge, HUGE clue that creeping featurism isn't always an advantage. Quite the contrary.