Python 2's approach was bad, no argument, but the transition plan for 2-to-3 just didn't work. They thought everyone would run 2to3 in a big bang, and then we'd

Python 2's approach was bad, no argument, but the transition plan for 2-to-3 just didn't work. They thought everyone would run 2to3 in a big bang, and then we'd all switch over to 3 in a few years. Instead it dragged out over a decade because in reality we needed to write code that was compatible with both 2 and 3 (the "6" approach) until enough things were on 3 to drop 2 support. Hindsight is 20/20 naturally, but in retrospect, they should have just made `bytes` into the name for old `str` and used `from __future__ import` to create a gradual system for moving from 2 to 3 instead of a big bang "we'll break everything once and then never again".