[inferiorhuman]

By far the biggest thing for me is package/environment management. All of the tools I've used just suck. Pip, virtualenv, conda. For me, at least, getting started with anything non-trivial in Python involves grinding my teeth and slogging through whatever unpleasantries. Recently I've run into problems where some stuff seems to not work between different minor versions of Python 3. Ruby is generally easier and more portable – that a large subset of Python folks have standardized on a model / management tool like Conda that's not portable is something I can't say anything civil about. I can't think of any other language that's done something so boneheaded.

Beyond that Python is opinionated. In a lot of ways this is an improvement over e.g. Perl. However enjoyment is largely predicated on liking the opinions, if you don't it's not fun. For instance I wanted to write a multi-line lambda recently (mostly to make it easier to read). With Ruby and Rust I can do this pretty easily. With Python? No dice. Sure, there are good reasons to not make a lambda a multi-line ordeal but sometimes I just want to.