Feels like we remember MS-DOS as simple because it fit the time. One user, limited hardware, not much going on in the background. As soon as you try to add multitasking, networking, or even basic isolation, that simplicity doesn’t really hold up.
MS-DOS was quite simple if you think about it.
Past that point complexity kept on increasing. Don't get me wrong - I use modern day linux, modern day ruby ... it's all fine. Modern computers are fast too. But at the same time I feel we lost simplicity along the way. Now this is even more noticable with microslop everywhere.
But OS/2 was a better DOS than DOS, and a better Windows than Windows!
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Fun fact, while Trower was the manager who got Windows moving, it was Gabe Newell who served as the lead developer of Windows versions 1, 2, and 3. Win95 was the first version he wasn’t really involved with. By that time, he was working on porting Doom to Windows.