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Windows 3.0 won 'cause Microsoft convinced everyone that 1MB would be enough memory to run a windowing system (and it was, if one had one written in assembly language such as GEOS).
People bought Windows 3.0, then bought more memory, then bought a memory manager, then bought a drive compression program, then bought a larger hard drive, then Windows 95 came out and they started the whole thing again, 'cept w/ 4MB RAM.
OS/2 was quite nice, the problem was IBM was more realistic up front about the memory requirements, so it was perceived as much more expensive.
I'd give a lot to be able to find a copy of OS/2 for Pens which was updated for Y2K.
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