Okay, so taking into account everyone's suggestions, and attempting to come up with an appropriately difficult first day, you get... this.
Today, Team Expo needs to come up with
A) Gundam cosplay (as in a giant robot, not an emo pilot)
B) Crossplay of some sort
C) Open ended prompt: Tentacles. Don't ask, don't tell, but I want pictures of tentacles.
Team Expo: Well, there you go. That shouldn't be too hard for day one, should it?
Home Team: More ideas! Tomorrow morning I'll do this again, and post their findings.
1 I think i was one of the first on this site to put pics like that on the site :)
2 Bit hard to find good ones that aren't to creepy so I`ll post mine later XD
3 I should just pm you the link of my fav H picture site for that one >>
Edit: Correction from looking at the gallery i was in fact not the first to do that ^^
The "Biggest" cosplayer. (in wight)
Crossplay of a character who is a cross dresser. (yeah that one is a bit confusing)
A costume that take 2 people to pull off.
@Moonstorm: I love the 2 person one. Totally putting that in either tomorrow or Saturday.
@Schwindelmagier: I love the idea, though I question if they could find it. Also, depending on who they are it might be hard to spot.
I wanna see a buff cosplayer without a shirt on like Kamina or Dante or something. And the cosplayer should be buff not some scrawny kid please :P
Older anime that people should know *cough*Fist*coughcough*NorthStar*cough*
Anything that makes Kuro flip, either up or down.