This was a doozy to try and wrap my head around, but once I did it was extremely intriguing. I like the back-and-forth between the characters and the writer, and how the writer seems afraid of how to present a character, any character, for fear of social backlash and inadvertent stereotyping. Your piece reads almost like a stream of consciousness, tracking the thought process of the writer through his conversations with the characters. Meta-fiction isn't something written often, and I appreciate the creativity it took to attempt a meta-fictive story of your own.
I'm guessing your word count stopped at 300 because you didn't know where to take this. What is the point you are trying to make with this? Think about what you wanted to do with this story and follow it to its logical conclusion. You could focus more on the writer as a conclusion, with introspection and commentary, or continue your pattern of focusing on various characters and examining the flaws in their creation. You have intimidation as a consistent theme in each of your scenarios, so try flipping it on its head and analysing it. What do we consider intimidating? Why is it intimidating? How can you continue the pattern, and how does it relate to the writer's fear of creating a "problematic" character, and of social backlash?
I like what you've written! Keep going with it and I'm sure you'll do well.
