I can’t believe I got back to this point. Honestly, I worked my ass off for this. I’m so proud of myself.

I actually like the idea of a collaborative critique based competition. Something like all entrants submit a piece and are assigned some number of randomly selected participants who have to work with them to help develop their piece. The winner is the person who's piece shows the greatest level of improvement (decided by popular vote) rather than the "best" overall piece. Probably their assigned buddies would also get some share of the glory.

I feel like any outright competition undermines the ultimate goals of the site to a degree, but something like this would support our values.

This sounds great. I want!

Now that I think about it: In another forum I was active a long time (ago) there was a pool of giveaways for forum activities like quizes and stuff. Everyone was able to spend for this pool. We shared old video games, shirts, figurines... it was a german community though. The shipping costs for these giveaways were paid by the new owner. It might not work this way in a world wide community.
The giveaways were ranked with points. For example, a winner of any contest could choose one gift for three points or three gifts for one.

It was quite an interesting concept.

For some reason the first game that came to my mind as I red this was "Super Mario Land 3: Wario Land". And my memory hasn't tricked me.
There are some areas that look a little emtpy, but others really look good.