This reminds me of college, when some of my professors were still sorting out their curriculum and would give us homework assignments with bugs in it.

I complained many times that they were enabling my innate procrastination by proving over and over again that starting the homework early meant you would get screwed. Every time I'd wait until the people in the forum started sounding optimistic before even looking at the problem statement.

I still think I'd like to have a web of trust system where I let my friends try out software updates first before I do, and my relatives let me try them out before they do.

Ah, I remember those days. One that wasn't an error exactly was an assignment that had a word limit of 2000 words or something. I'd written maybe 3000 words and spent quite some time cutting it down, getting it to just under the limit. Then someone else who also wrote too many words asked the professor if that was okay and they sent out an update to everyone saying it's fine to ignore the word limit.

For windows updates r/sysadmin has people who run updates and post their experience on patch Tuesday.