IDK, I just have never really had this become a serious issue for me. I get what you mean, some actions are a little bit of a pain in the neck because people are often sloppy about typing, but literally the only time I can remember it being an issue at all has been when numpy is involved and so I have to figure out if something is a native Python thing or a numpy-fied custom structure.
I mean there's just not that many types. Generally something is a list, a number, a map, or a string, and it's pretty obvious which. Maybe there are OOP domain things where a lot of variables are objects of some kind of class (sort of more of a C++ type of program structure), and so it starts to become really critical to have strong type tools, I'm just saying I haven't really encountered too much trouble with it. I'm not saying it's imaginary, you may be right in your experience, I'm just saying I've worked on projects way bigger than a few hundred lines and never really had too much of an issue with it in practice in my experience.
It is clear that this horse knows what he's doing. Just give him oats and fillies and let him run around and do his thing. Humans are fuckin' weird.