It is too broad. From What types of questions should I avoid asking?:
You should only ask practical, answerable questions based on actual problems that you face. Chatty, open-ended questions diminish the usefulness of our site and push other questions off the front page.
This question you've asked is the second kind of question. It is not actually a question with a single best solution or answer available, but instead it is a prompt for a discussion, or a survey of peoples' thoughts. It is a good prompt and might lead to quite a great discussion! It just produces a question that is not very viable in Stack Exchange's Q&A format.
This warning also applies:
To prevent your question from being flagged and possibly removed, avoid asking subjective questions where …
- every answer is equally valid: “What’s your favorite ______?”
It is almost certain that this question would attract an endless list of answers, all equally valid, by people listing one or more challenges basically forever. Very few would be better or more correct than any other, because they are all people listing challenges, which is what was asked for. This is what makes it a survey.
It makes matters a bit worse that you are trying to collect all possible challenges in all possible reasonable interpretations of “chaotic evil” in all possible games that provide anything like that kind of thing, but even if you scoped it down to just one game and edition (e.g. D&D 5e) it would still remain a survey and would be closed as too broad.
Instead I recommend asking this question on one of these forums we'd recommend and come to us when you have a specific game with specific problems with a specific chaotic evil character (or player who wants to play one).