I suppose if you're dealing with a large company that has lawyers on staff but doesn't care about user support, then this is a good avenue. Small companies and non-VC backed startups on the other hand wouldn't see it as playful.
So, contextually, I can see a situation where your perspective makes sense. Like those situations where you can imagine a corporate lawyer laughing at you for taking them to small claims over a username. You just need to read the room and know when it'd be good fun vs when it would cause problems.
Oh, and you also need to have enough money for expensive hobbies. The subset of users who are in a position to engage with companies this way probably differs significantly in many ways from the total population of users, assuming a popular product.