The last month or so, I've been watching a lot of clabretro's videos. If you find this sort of thing interesting (old enterprise software, and possibly the old servers/equipment that would run that software), you'll definitely like his channel! His retrorack is more from the early 2000s rather than the late 2000s, but there's probably still a good amount of cross over between what you're both doing.

https://www.youtube.com/@clabretro

Funny; Vista was the reason I switched to Linux as well.

It doesn’t feel that 2009 is all that far away but… 17 years ago. I remember a lot of forums during 09” in fringe commodore groups and amiga. And they still go on.

But yes 2009 was a different time, to be a sysadmin all you had to effectively know was how to reinstall an OS and drivers and you were golden.