I find it amusing that you use the example of Python 2 -> Python 3, a breaking change in a widely used language, that has famously been very difficult and long for organisations to deal with.
Compare that with javascript which has never had a breaking change. On top of that Typescript is a backwards compatible superset of javascript.
More to the point, Ryan has a humble explanation of what regrets he has about Node.js[1], why they exist and in some cases why there isn't an easy fix.
The point that I assume you're making, that sometimes it is better to spend significant energy to fix something, rather than throwing the baby out with the bath water, is a good one. However I'd suggest this is not one of those cases.
Compare that with javascript which has never had a breaking change. On top of that Typescript is a backwards compatible superset of javascript.
More to the point, Ryan has a humble explanation of what regrets he has about Node.js[1], why they exist and in some cases why there isn't an easy fix.
The point that I assume you're making, that sometimes it is better to spend significant energy to fix something, rather than throwing the baby out with the bath water, is a good one. However I'd suggest this is not one of those cases.
[1] https://www.youtube.com/watch?v=M3BM9TB-8yA