I like typing in Python because I can choose how much I want to use it. If I want to script something, or prototype something, or test something in a repl, no overhead of typing needed.

It's also been my experience (C(++), Kotlin, Swift) that as the complexity of typing increases, 10% of the time I spend servicing types accounts for 90% of the sites I need typing, and the other 90% of the time spent on types is me cursing at the compiler trying to make it accept the odd 10%.

An optional type annotation system allows ME to pick where I want that effort/payback balance to be at on a case by case basis.