Pip and venv have been tools that I’ve found to greatly accelerate dev setup and application deployment.

I'm not saying pip and venv are worse than not using them. They're obviously mandatory for Python development. I mean that compared to other languages they provide a pretty awful experience and you'll constantly be fighting them. Here's some examples:

• Pip is super slow. I recently discovered uv which is written in Rust and consequently is about 10x faster (57s to 7s in my case).
• Pip gives terrible error messages. For example it assumes all version resolution failures are due to requirements conflicts, when actually it can be due to Python version requirements too so you get insane messages like "Requirement foo >= 2.0 conflicts with requirement foo == 2.0". Yeah really.
• You can't install multiple versions of the same dependency, so you end up in dependency resolution hell (depA depends on foo >= 3 but depB depends on foo <= 2).
• No namespace support for package names so you can't securely use private PyPI repositories.
• To make static typing work properly with Pyright and venv and everything you need some insane command like pip install --conf-settings editable-mode=compat --editable ./mypackage. How user friendly. Apparently when they changed how editable packages were installed they were warned that it would break all static tooling but did it anyway. Good job guys.
• When you install an editable package in a venv it dumps a load of stuff in the package directory, which means you can't do it twice to two different venvs.
• The fact that you have to use venvs in the first place is a pain. Don't need that with Deno.

There's so much more but this is just what I can remember off the top of my head. If you haven't run into these things just be glad your Python usage is simple enough that you've been lucky!

I’m actually in the process of making such a push where I’m at, for the first time in my career

Good luck!