> So if my email is HeLLo@example.com because I want to be cute people will have to try 6 times before they finally get the right email address? Imagine telling that to someone in person.

Yeah. That's fine.

If my email is LLLLLLLLLLLL@example.com because I want to be cute I have to tell people to type exactly the right number of L's. Do you think they should just be able to type a lot of L's and as long as it's somewhere near it counts as the same email address?

In a world where email addresses are always case sensitive, everyone will use lowercase (like they pretty much always already do anyway), and it'll be fine.