I've maintained technical debt ridden code for most of my career - initially in C#, Javascript, also doing PHP and Java. Python is the only language for which it was remotely bearable.

It has some warts (it is weakly typed in some respects) but the only languages that fix those warts have a pale shadow of Python's ecosystem and you typically cannot prototype as fast in them.

As for tooling, it's probably got the best REPL (IPython) of any language.