Not allowing strings to represent invalid Unicode is also a huge mistake (and essentially forced by the representation strategy that they adopted). It forces any programmer who wants to robustly handle potentially invalid string data to use byte vectors instead. Which is exactly what they did with OS paths, but that's far from the only place you can get invalid strings. You can get invalid strings almost anywhere! Worse, since it's incredibly inconvenient to work with byte vectors when you want to do stringlike stuff, no one does it unless forced to, so this design choice effectively guarantees that all Python code that works with strings will blow up if it encounters anything invalid—which is a very common occurrence.
If only there was a type that behaves like a string and supports all the handy string operations but which handles invalid data gracefully. Then you could write robust string code conveniently. But at that point, you should just make that the standard string type! This isn't hypothetical, it's exactly how Burnt Sushi's bstr type [1] works in Rust and how the standard String type works in Julia.