Again as a casual user, I don't want to state anything too strongly, because some of it could be user error... but a few of the troubles I've had just trying to

Again as a casual user, I don't want to state anything too strongly, because some of it could be user error... but a few of the troubles I've had just trying to use and update Python in the last couple of years include packages from PyPI being broken and refusing to install; this including pip so pip was not able to update itself. Packages with dependencies that won't install from PyPI (or installation fails on my machine), sending you looking for tarballs. No clear route to upgrade between semi-major versions of Python. Things that install but need the config frobbing before they work - I'm not afraid of doing that but it's always a hassle. I think some of the problems were self-inflicted by trying to use Python on a Mac with no package manager, and on Windows. Things will get easier on the Linux side with Python 3 in repositories now. But it really seems like a fairly common pattern for languages / programming environments is to install the languages package manager and upgrade packages separately from the OS package manager. For whatever reason this seems like a bigger headache with Python than others.