uWSGI is a lot of joy for me, really, I've never been happier with my deployments since I have discovered uWSGI back in 2008 or something, and nowadays it supports plenty of languages so there's just nothing I don't deploy on uWSGI anymore.
Python packaging is something that I have fully automated (maintaining over 50 packages here) and that I'm pretty happy with.
I fail to see the problem with Python packaging, maybe because I have an aggressive continuous integration practice ? (always integrate upstream changes, contribute to dependencies that I need, and when I'm not doing TDD it's only because I have not yet proof that the code I'm writing is not actually going to be useful) That's not something everybody wants to do (I don't understand their reasoning though).
People would rather freeze their dependencies and then cry because upgrading is a lot of work, instead of upgrading at the rhythm of upstream releases. If other packages managers or other languages have packaging features that encourages what I consider to be non-continuous integration then good for them, but that's not how a hacker like me wants to work, being able to "ignore upstream releases" is not a good feature, it made me a sad developer really, "ignoring non-latest releases" have made me a really happy developer.
Most performance issues are not imputable to the language. If they are, it's probably not affecting all your features, you can still rewrite the feature that Python is not well performing for into a compiled language. I need most of my code to be easy to manipulate, and very little of it to actually outperform Python.
I've recently re-assessed if I should keep going with Python for another 10 years, tried a bunch of languages, frameworks, at the end of the month I still wanted a language that easy to manipulate with basic text tools, that's sufficiently easy so that I can onboard junior collegues on my tools, that provides sufficiently advanced OOP because I find it efficient to structure and reuse code.
Python does what it claims, it solves a basic human-computer problem, let's face it: it's here to stay and shine, and its wide ecosystem seems like a solid proof. Wether it makes sense to invest in a project or not should not depend in the language anyway.