> In an era when people still paid money for operating system upgrades every few years (anyone else remember standing in line for Windows 95?)
No, and I would have been too young to purchase it.
But I'd be surprised at the idea of massive demand for an upgrade to Windows 95. What we did was buy a new computer that had Windows 95 on it. Computers used to go out of date very quickly.
We kept our older computer that ran DOS. (It had Windows 3.1 installed, but the only reason you'd start that was if you wanted to play Solitaire.) It continued to run DOS just fine.