[jbbarth]

I'd say Python tooling may be OK at language level, even slightly better (code introspection abilities are more recent in ruby I think, the fact you could get method docs, method def, etc.). The equivalent for IPython (shell version, not notebooks) in Ruby is pry and it's pretty good.

On the other side, in Python higher-level tools are horrible from an operational perspective, and much worse than Ruby's if you ask me (pip vs bundler, rbtrace vs.. gdb-python(?), pry/pry_remote vs pdb, ...).

Also +1 on boardwaalk's comment, this side of Python is pretty good.

[krakensden]

Pip+virtualenv is great from an operational perspective- it makes building tarballs to ship super easy.