Separately from my other comment, you said Python and Ruby are very similar in style and goal, and what are you overlooking? As someone who has done a decade o

Separately from my other comment, you said Python and Ruby are very similar in style and goal, and what are you overlooking? As someone who has done a decade of Rails development and works in a Ruby + Python shop, I'd say you haven't overlooked anything. Ruby and Python are so similar in style and tradeoffs that it's quite difficult to make a case for one _language_ over the other for any particular task. So then it comes down to (1) ecosystem and (2) personal preference. For a long-time Ruby has had a better web ecosystem. I'd argue this is still true, but I don't know if it will last. The reason is that Python's overall ecosystem has developed a lot more than Ruby's and the overall larger community is really valuable.