[davidjfelix]

My opinion is there were 2 major issues and a bunch of minor cuts.

The major issues (imo):

* Reliance on extending the runtime via the C-bindings (and that changing)

* A community that had largely gotten accustomed to stability being thrust into an enormous change all at once

I think people tend to be in a camp of either "this was good and needed to happen because python had unshakable warts" or "this was bad and we should have lived with language mistakes forever". I think both of those camps conflicting is really what made it really painful - breaking changes were held for years and then once one got in they all came. I think the reality is that coming up with a migration plan incrementally working towards it would give developers more time to focus on one upgrade rather than a full rewrite. Node gets a bad reputation for being "chaotic" or "constantly changing" but the changes are small and manageable comparatively. Go on the other hand has managed to maintain strong stability, but with an ecosystem that's working primarily in the core language rather than the implementation language (C for python).

I think the python 3 merge did a ton of damage to the community's willingness to encourage breaking changes that are needed and it's why packaging and runtime self hosting have been comparatively weak despite a huge userbase.

Not breaking apis is a great ideal but if you have to, breaking them in planned, bite-sized, frequent bursts is often MUCH MUCH better than once a decade.

[AlotOfReading]

I finished what will hopefully be my last 2->3 transition ever back in 2021. 6 months, ~180 commits, and 3,000-odd files in that single PR, after years of preparatory work by others. I needed a sabbatical after that.