The MAX_PATH limit is annoying legacy backwards compatible stuff, but can be avoided by prefixing paths with \\?\ before passing them into the Windows API.

This is something that languages/runtimes with more effort put into portability already handle for you:

https://github.com/openjdk/jdk/blob/master/src/java.base/win...

If Python doesn't do this it's just because the sort of people who write Python don't care about Windows enough to fix it.