For me, it's always frustrating to have to guess the types of parameters in functions without appropriate documentation, especially considering that I don't know much of the language.
Combined with the fact that static analyzers for Python can very easily get slow (ex. completions for Tensorflow always take multiple seconds, which IMO is unacceptable), it's just not something that makes the language seem like a reasonable choice to me.
I was working on Tensorflow bindings for Dart, which is Java-level statically-typed now, and in porting functions from Python found myself absolutely lost as to what any of the code actually did.
I might be the only one who dislikes Python to this degree, though.