venv has been included with Python since 3.3 (2012) and was a separate package before that. If you're having troubles with the ecosystem playing well with Python 2.6 (2008) what do you expect anyone to do? I really think OS package managers have been really negligent about multiple versions and project-level dependencies--maybe it's outside of their scope (that also wouldn't help you on Windows)? People have been griping about software specific package managers for over a decade and OS package managers have only added the most minimal support, but never addressed the reason for them.
I've argued for years, if something is critical to your business then decouple it from the OS. Of course a new version might screw up your OS and you may need it to address a specific business concern...that's just one of the problems of any interpreted language. I wish things were better out of the box, but it's not unreasonable to address yourself.
node vs web browser? linux vs unix? ubuntu vs debian? autotools vs base make?
i'm sure these aren't the best examples.
irrespective, you can (like|dislake) the language and (like|dislike) the ecosystem separately.
"oh I hate programming in XYZ it's far too verbose but it really does have a nice package management system"
yes, they are connected, but I don't criticize a hamburger by complaining about the taste of my soda..
Regarding 1: I'm sick of people saying that the ecosystem != the language. No one is going to be able to prop up an alternative ecosystem and get more traction than the language's own ecosystem, so you are basically always stuck with whatever crazy ecosystem comes with the language. Most of what people care about is the ecosystem and the syntactic sugar relationship the ecosystem has with the language, so it is a very real criticism imo if a major programming language has a bad ecosystem.
You are stuck with the ecosystem you ship with the language, so get it right the first time.