I'll share my own story of the Windows 3.1 -> 95 migration and MS Tech support. At the time, I was using my grandfather's old PC that had originally been a 486sx 33mhz processor with 4mb of RAM and a 200mb HDD. We upgraded the machine using an Intel "Overdrive" processor to a 486dx/2 66mhz processor with 8mb of RAM and added a Soundblaster 16 sound card and triple-speed CD ROM drive. I received a copy of Windows 95 for Christmas 1995 and proceeded to install it on the system. It worked pretty well and, a few months later, I decided I wanted to add the "MS Plus!" pack.

I was 14 years old and knew very little about PCs at the time; though, I was learning. What I definitely didn't know at the time was that the HDD in the machine that I was told was nearly 500MB was actually a 200mb drive that had been compressed with an older version of DriveSpace. The addition of Plus! upgraded the compression to DriveSpace 3 which corrupted something on the drive that caused the system to hardlock as soon as the Windows 95 UI appeared no matter what I did.

After spending 4-5 hours on the phone with a very patient tech support specialist at MS, he eventually concluded that I would need to format the drive as nothing we did in those hours worked at all. Definitely a major learning experience for me doing my first full system format and OS reinstall.

By the end of 1996, I'd be doing my first Linux installation on a slightly newer PC that I saved money from a summer job to buy. If it hadn't been for DriveSpace 3 and an MS tech support specialist who educated the hell out of me for a few hours, who knows when (or even if) I would have gone down the rabbit hole that led to my career.