1. Do you think this would be a good idea? Why or why not?
No. I think everyone should be able to enter the contests. I’ve seen numerous examples of successful authors entering a well loved story but not actually win the contest shelf while newer authors or authors waiting to be discovered have won.
2. Do you think contests are for smaller authors to benefit? Why?
Well, not specifically but they certainly can be! I think entering a contest is a great experience for newer authors. You meet a lot of people and get to network, get your name out there even if you don’t win, etc.
You can make it a beneficial experience for yourself 
3. If you’re an author with more of a readership (I know this is a vague thing, but for the sake of this discussion let’s say if you have 100k+ reads) do you feel awkward/bad about entering contests because of this?
Ha! I have 124k reads and still feel like I am a small fry 
So…no!
4. Additional thoughts?
I entered the college day contest when I was still an episode newbie. I didn’t win but it was an amazing experience and I really did get to talk to a lot of people and start getting my name out there.
It’s also important to remember that just because you didn’t win, your story might still get the chance to shine later! Long after the contest was over, my story actually made it on to the epy academy shelf week.
Write something you want to write and you want to continue writing afterwards!