Surely you meant "OS with a significant market share" or something, because there's no way Windows is more "open" in any way than Linux!
Quite a lot of the core tools (shellutils) are 20+ years old with only minor updates.
Look, I'm not saying there is no Linux software that doesn't keep working, it's the overall time you spend over the lifetime of your software to keep up with updates in its dependencies. I don't see how anyone can reasonably argue that Windows isn't a whole lot better than Linux at that.
(I've been using Linux since 1998, I'm not new to this game)
My colleague is wondering how can he install latest copies of Office and Visual Studio Express on Windows XP SP2 for quite some time, without success.
Reliable platform means, that new versions of OS do not break your old program. Which is true for windows.
Of course, as OS becomes more capable, it's possible to write programs that can't work on less capable older versions. But even then, windows tries to add fallbacks so that most new programs still work on old versions.
The secret to being able to do this properly is to keep a curated development environment that has the old tools/libs in their proper form -- which I suspect is why you don't have a problem (20 years ago you had VC5/VB5 - do you compile the same program with VS2013?).
YMMV, but my experience is that the Microsoft environment is worse than Linux in this regard.
Didn't Win 8 jetisson most of the compatibility?
The parent to you is correct in that you can compile really really really old software on Windows with ease and very few changes. This is not possible on Linux.
Of course, that's because the libraries in fashion change on Linux very quickly and nobody cares about backwards compatibility that much. They say "just grab the latest version!" or "why are you trying to compile such OLD software?!", particularly if written in C or C++. I don't know about Python or scripting language support.
But a rubbish installer written by a company that has much of its UI written in Java (last time I checked years ago) doesn't really compare to the excellent backwards-compatibility of the Windows API and surrounding libraries.
This isn't even an anti-Linux rant; the same problem is found on Mac OSX. That runs into both problems - impossible to run old software (Rosetta support please?!) and impossible to compile it because the system has changed so much.