I inherited a couple of Python 2.7 projects recently and after many years of toying with it I'm finally using Python seriously. Well, the syntax of the language is a mix of strange decisions. Part functional, part object oriented, not well designed in any of those parts. The so old school looking special __functions__. The annoying syntax errors one gets when refactoring and moving code around courtesy of the useless : and significant spacing. The even more annoying indentation errors when copy pasting code from the editor to the interactive interpreter. ["a", "b"].join(".") and ".".split("a.b") or other permutations, I still can't remember which one is correct. It's not a very inviting home to live in, a kind of non euclidean space.
It's strange that Python got where it is today. Maybe it's because among the languages that were big 10 years ago it's more immediate to work with than Java an C++, because PHP is despised by many professionals especially pre v7 when it was really ugly, because nobody bothered to build and maintain a numpy for Ruby and because JavaScript become big only recently. I feel that Python is good enough to do almost everything but not particularly nice to look at.
However I want to end on a lighter note quoting Matz. "No language can be perfect for everyone. I tried to make Ruby perfect for me, but maybe it's not perfect for you. The perfect language for Guido van Rossum is probably Python."