I did not intend to imply that I'm
regularly writing code that's hard to justify to a type checker. In fact, most of the code I write is in statically typed languages (I'm not some kind of dynamic typing zealot), so I tend to avoid situations that could never typecheck before they occur.
However, I like to use Python for small single-purpose utilities, and in those cases I don't even bother with the optional type annotations, let alone checking them with mypy. Since those programs are so simple that a handful of test cases is enough for 100% path coverage, if the program runs correctly on one case, it's almost guaranteed to run correctly for all others. (Similar to Haskell's "if it compiles, it runs".) Statically checking for type correctness would be pointless, because you can just run the program to find out. It then becomes quite natural to e.g. apply type-modifying transformations in-place, which most type checkers wouldn't allow, since they assume a single fixed type rather than a progression of different types during different stages. (You can get around that, of course, but it requires constantly recreating essentially identical objects to give them a new type.)
For an example of a project (not written by me) where the type checker's rejection of a correctly working program precluded the use of a type checker, see http://www.oilshell.org/blog/2016/11/30.html