This doesn't answer your questions, but I firmly believe this is the major reason node took off in popularity.
Npm let you install packages minutes after being installed, and they went right into a folder right there, and they didn't conflict with any other packages on your system.
I was like you and played with python for years but never anything larger than small scripts, and every time I went to do "real" python I'd hit a wall where you were.
npm was just so easy, so simple, so fast that it won me over. And it was years before I ever setup a virtualenv, and even then I'm still at this point not entirely sure how it works and what it's doing despite having published a pip package.