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For the Trick-or-Treat Wonderland contest, I had the main aspects in bold. I wanted to see both Wonderland and Trick-or-Treating. That meant that the character would need to have some candy, maybe a costume, or a pail (or whatever that character would collect candy with), or.. since this is Wonderland, maybe they were collecting tea instead? You never know. XD; But I wanted to see some attempt at collecting or asking for something that made sense in Wonderland.
Next, character (and with that, how much effort was put into the look). (Actually, I held Wonderland a bit higher than the Halloween aspect, but they were about equal.) With your entry, I loved the arms! That was a great idea to be the Caterpillar's cousin! But then.. the idea strayed from there. I'd liked to have seen butterfly wings instead, to reinforce the connection to a caterpillar. Wonderland is a kooky place, but each individual character holds true to what it is. (I believe the most mishmashed character is the Gryphon, but he even holds true to a griffin stereotype.) So a caterpillar keeps butterfly wings, not angel wings. I get that the pile of gold went with your rich theme, but that didn't connect into Halloween. And I got that the crown went with your rich theme, but XD; I'm pretty sure the Queen would've had your head already for attempting to wear a crown. ;D Blasphemy! Off with your head!
Here's my interpretation of the Caterpillar's rich and benevolent cousin:


And for the Up the Rabbit Hole contest, I put in bold words that I needed classic, generic Halloween characters. And then listed examples of what I consider to be classic, generic Halloween characters. You know, the types of monsters and such that you see every Halloween and on many of the Halloween decorations.
A mutant king and Avengers aren't classic Halloween monsters/characters. They could fall into costumes that a lot of kids wear for Halloween, but Avengers don't represent Halloween. Just like how a lot of people dress up as nurses, but nurses don't represent Halloween.
For this contest, I was looking for a classic monster/character, thennn how /classic/ that monster was to the stereotype. I didn't ask for the stereotypes to be reinvented. If someone gave me Frankenstein (or, rather, Frankenstein's monster for those picky people), I'd be looking for tattered clothing, bolts, maybe flat hair, scars, even patched skin. Gaia has lots of those items.
Past that, if people gave me a cohesive character that fit stereotypes and accessories to reinforce the stereotypes, theeennn ties get broken by 'how good' their avatars look.


So with my contests, I usually /hint/ at what I'm judging on by putting those words in bold. The closer users get to those bold words, the higher the rating. The more items that take away from a theme, the more it drops out of the running. I don't actually tally up the number of items, but how much impact those items have on the overall look/theme.
Avatar contest hosts don't usually put what they want in bold, but they usually give a pretty good description of what they're looking for. ... But I'd venture to say that, unless they're really stressing a theme, "looks" are most important. In those cases, it starts going into details. Layering and details. And faces. You usually need to add a bunch of details to fill in any empty spaces. ...unless it goes against theme.

I decided to play with the concept more and got these XD;