It has been about 10 years since Python was a daily driver for me and at that time I wrote it the old fashioned way with no type hints and no static checking, just like grandma used to make. The times I have needed to dig back into it have involved working on old code, so I haven't kept up with modern tooling.

However, in principle any dynamically typed language can be tolerable to me if it can be turned into a statically typed language ;)

But I think I'd still prefer the ergonomics of a language designed that way from the start vs having bolt-ons. My favorite language for the past several years has been F# and I think ML-family languages in general strike a great balance of being able to write terse code when you want to, and being able to model a domain really well with types when you want to.