For me, the Ruby community's comfort with monkey patching was a big turn off. In Python, you can hack around on class and replace its methods, but if you do, it's expected that your coworkers might stick you in a dunk tank and sell tickets. It's just not the thing that's done.
Monkeypatching is maybe more of a Rails thing than Ruby. I think the biggest problems with Ruby around the time Python began to take off were slowness (MRI was a disaster, slow, and full of memory leaks), plus patchy documentation (lots of things were in Japanese).
Still, I preferred and prefer Ruby. Python has fantastic libraries, but it is a mediocre language. Ruby feels like a simpler version of Perl + Smalltalk, and it is a joy to use. Python has intentionally crippled anonymous functions plus syntactic whitespace, which often leads to long and ugly code.
I think it is a shame Guido hated functional programming and he did not embrace an Algol-like syntax with begin/do end blocks. Those two things could have vastly improved Python. Ruby's block, procedure and lambda design is a stroke of genius that yields beautiful code and makes DSLs trivial.
For me, the Ruby community's comfort with monkey patching was a big turn off
If it helps, the Ruby community really soured on monkeypatching in general quite a while back. You don't see it much these days and every decent book or guide warns against it.
It was definitely a crazier place 10+ years ago in the early Rails days.
I certainly wouldn't blame a person for experiencing those crazier days and thinking the community didn't have the greatest technical vision.
I played around with Rails and Ruby when Rails first blew up. But I didn't start doing it fulltime professionally until 2014. By the time it seemed to me that the community was maturing. I think it's in a good place now.
An easy way to start taking the fight back to the enemy is by overriding __new__ and tinkering with things before/after Django's metaclass __new__ does its own metafoolery.
Also overriding mro() is a fun way to monkey with the inner workings.
