How would people that use both Python and Ruby compare the tooling for both languages? I only am familiar with Python, and I end up using IPython most of the time. I'm curious whether I'm missing out, or maybe Python also has "terrible" tooling..
This is pretty specific, but Ruby has pretty terrible support for parsing Ruby. Libraries are either unmaintained or broken or for old versions. Python is great for parsing ('import ast'), compiling ('compile(...)') and executing ('exec(...)'). So it's much easier to write code generators, write linters and autocompletion tools and such.
https://github.com/whitequark/parser
Neither unmaintained, broken nor just for old versions. It has some really minor incompatibilities though:
https://github.com/whitequark/parser#known-issues
The same person also wrote a Python parser because apparently the ast module doesn't provide precise location information of tokens: