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.