In my opinion, the biggest problem facing Python is still concurrency. The mitigation efforts still look to me like Perl's 'bolted on' implementation of object orientation. Python should have gotten rid of the GIL during the 2 to 3 transition. It may have also been an opportune moment to introduce optional typing and maybe even optional manual memory management, making it useful to develop almost all kinds of software. Write a WASM backend and it could have even been used for front end development.