same here. Been using python/pip for 10+ years and this was never a problem. In the java world, there is jar hell, but it was never a crippling issue, but a minor annoyance once a year or so.

In general, is dependency management such a massive problem it is made to be on HN? Maybe people here are doing far more complex/different things than I've done in the past 20 years

Guessing that folks who write such things are lacking sysad skills like manipulating paths, etc.

It does take Python expertise to fix other issues on occasion but they are fixable. Why I think flags like ‘pip —break-system-packages’ are silly. It’s an optimization for non-users over experienced ones.