[ranger_danger]

What kind of trouble? That's all I've ever used for the last 15 years of my professional Django work and never had any issues...

[Balinares]

Incompatibility with Python version in current LTS Ubuntu sounds like an issue to me.

FWIW I used to be fine with just dealing with system Python, like you, but recent tools like uv make it so easy and convenient to isolate interpreters and dependencies per project that I'm just not going back.

[stackskipton]

Anything involving Distro updating. There is no reason not to use containers except Docker Build scary!