So, FireCubes, I'd first like to talk about the biggest problem I see with your challenge: it's what I call a one-up challenge.
In essence, a one-up challenge is when the best bot can easily be beaten by one-upping them
The Lorem-ipsum is a perfect use case for this: If the best player is adding lorem ipsum, then all I need to do is add that to my guesser
but then another bot can come along and beat mine
and so on. It's impossible to make a bot that can't be trivially beaten