I have never been a Python fan, but I wrote my first python application in Zope 26 years ago it still runs. Since then I have touched other things that are much worse not all of them on the list above. My point is that while python may break, other stuff breaks as well.
There are a lot of prototype integration projects in Python though and that is incredibly hard to get running. I know nothing about C# but as Linus Torvalds said the binary compatibility layer for Linux is Win32 because of Steam, so MS has worked on the problem before. Though I would like to point out that when you are talking about prototype integration projects Windows is as bad as Python, I have rebuilt test environment in Windows that had been left to rot for ten years.
So in my work life experience all programming languages suck at this, python might suck less or more but it is more of a skill issues than anything.
There are a lot of prototype integration projects in Python though and that is incredibly hard to get running. I know nothing about C# but as Linus Torvalds said the binary compatibility layer for Linux is Win32 because of Steam, so MS has worked on the problem before. Though I would like to point out that when you are talking about prototype integration projects Windows is as bad as Python, I have rebuilt test environment in Windows that had been left to rot for ten years.
So in my work life experience all programming languages suck at this, python might suck less or more but it is more of a skill issues than anything.