Why is Python so hard to maintain

[metulburr]

Actually, doing ANYTHING in a command shell in a windows environment is not ease of use. This is not DOS!

That is up to interpretation. It probably just because you are not use to it. In Arch Linux for example, after you install the operating system. You have to install the desktop (IE. the GUI). And some people dont ever isntall a GUI as they consider it to be laggy. A lot of linux servers are terminal only. There is not need for GUI. One of the first things i do in Windows is bring up a command prompt to bypass the GUI.

Having to edit PATH variable in Windows to manage multiple versions.

I havent used Windows much in years so i could not say. Although doing anything in Windows takes forever in comparison to linux. I hate being in that operating system as everything is more work involved.

pip installing module in the wrong place (my Python37 not Python33)

That is because you invoked the python3.7 pip then. What reason do you have anyways of having all them installed? You can use a virtual environment to handle multiple python versions much easier.

redefining the syntax of a basic function between versions (print for example)

print was converted to a function in python3.x. This is commonly well known at this point.

redefining the type of the result of a library function between versions (struct.pack for example). very uncool.

One change between python3.x and python2.x was bytes and strings. Like with any language, if you are using C++14 syntax and try to compile it in a c++98 compiler you are going to get errors. The same is true with python2.x/python3.x interpreters.

The fact that you are referring to python3.x/2.x incompatibilities refers me to think that most of your issues are in conjunction with those versions. I would use a python3.x tutorial at this point for everything. Python2.x is dead soon.