I am a fan of Vista, but 95 was my gateway drug to tech. I remember when I was like, 4? And I discovered that exes were like, huge! But lnks, tiny! Why do we have all these space-hogging exes anyway? Begone! Look dad, I saved us so much drive space! Why does nothing work now?
And that's basically been my method of learning ever since. How much can you really break, before it's broken, and why? Let's find out!
I used to mess with my windows Millenium so much and deleting random files and changing regex and understanding how things worked that tech support guy was almost every 2 weeks there reinstalling the system for me. And that was how they started to give me copies of the cds to install myself so I wouldn't bother them so much.
Getting the windows ME installation disks (floppys) was how I started learning my way around computers. I could experiment with the registry and other files and if I broke something I could just to re install the OS
Vista did a bunch of great things... It added BitLocker drive encryption. It added the Snipping Tool for screenshots. It added a newer driver model that end up making drivers far more reliable than on Windows 9x and XP. It required drivers to be signed, which helps a lot with security. It added UAC, which was initially painful but also really helped improve security (no more running every single process with admin permissions). It moved C:\Documents and Settings\ to C:\Users so we didn't have to type that long path any more. And probably a bunch of others I'm forgetting
It was kinda half-baked at the time, but these are all major defining features of Windows. It just took a while for them to become stable.
Self-healing capabilities, and the ability to do an 'in-place upgrade' (installing win over itself without data loss) were huge too. I had to wipe + reinstall XP dozens of times throughout the years, often for some small bullshit. I was a Vista beta tester, and got a copy for my machine as soon as it went gold. I went all-in and it was actually a fantastic OS. 7 was good too, but it didn't do that much new, comparatively. It stood on the shoulders of giants.