[dtech]

For Windows you can, but Microsoft is diversifying risks and running their software on other OS and hardware, and Office is a major windows-independent revenue stream.

So I'd say 2020 -> 2040 Microsoft is a safer bet than 1996 -> 2016 Microsoft.

[ralfd]

I think it is riskier. Microsoft in 1997 had virtually no competitors. That is not the case anymore.