&gt; packaging and deployment in python remains such an amazing mess, even after 20 years.<p>I&#x27;m Lua fanboy, but I&#x27;ve to admit, that I&#x27;m missing clean deployments and upgrades with virtualenv and pypi available in Pyhton. I&#x27;ve never had any issue so far, am I being just lucky bastard? It has been like that for many years already.<p>&gt; Ruby has better tooling libraries<p>On the other hand, I&#x27;ve honest to maintain one Redmine instance (which is written in Ruby) and this is real nightmare for me. Each time I&#x27;ve to upgrade, I&#x27;ve to drink a lot day or two in advance :-)