This part doesn't seem quite right--people don't know what they're going up against when they submit. If someone submits a 4 screen map against a full overworld, is that actually because they wanted to do that?
Totally fair, no one has that kind of foresight. When entering Map of the Month you should always expect a submission that's bigger than yours. I don't really anticipate many four screen maps to be submitted throughout the entirety of the contest. There's really not that many areas in projects that are four screens big to begin with. I'm for anything being submitted each month, but I am looking to see what the community feels here... they are the reason the contest will become alive again after all.
I guess I'm concerned about too many brackets. That kind of thing feels more fitting for something that's weekly like Screenshot: Challenge Accepted. One could potentially wait almost a quarter of a year to submit their dungeon map and that's assuming that there will be enough dungeon maps for that themed Map of the Month to happen. And even then, this won't exactly achieve a fair outcome as who's to say someone won't make a giant single area?
I just feel a little unfairness is always bound to happen in a contest environment. And ultimately, what should matter more is having fun and showing off cool ZC maps you recently made or want to reflect on. I'm not going to discount more brackets if people want that, I just don't quite have the same level of confidence some people might have for it. But the proof is in the pudding and I am willing to experiment to see the results.