It really sounds like your code base simply wasn't too big after all. When you change a Java API, how much time does it cost you to find all broken client code? How much in the same case for python?
> Frankly, I think velocity is ridiculously underrated
Again, it sounds like your projects were still rather young. IME, throwing away code practically never happens when it has been installed for at least half a dozen customers. So python helps you to build stuff quicker, because it does not force you to be sound. But soundness is exactly what you want after a certain threshold.