I agree: I think most people that look at typechecking as a serious friction are thinking about it wrong; the problem is probably languages with bad ergonomics. Many people who use TypeScript actually end up using it with strict defaults for even new or toy projects - it’s too valuable to not, honestly.
Another aspect of that which I have noticed is that so many fans of dynamic languages refuse to use IDEs. They'll even state it simply as "I don't want to use a language that makes me use an IDE". For me, the IDE is like a second part of my brain. I use Eclipse which does incremental compile at every keystroke and I see errors, warnings, autocompletes, hints etc in real time. This removes a huge amount of the ergonomic barrier they are talking about (having to save your file, run a compiler, only then see the errors, then find that line in the file, etc ...). But they are stuck at "I don't want to use an IDE" ....