There's also the little issue of using characters for something semi-official without seeming exclusionary. Like, TVTropes is emphatically "whatever goes" territory to me, but for the wiki...
Eh, okay, I guess it's history time. See, in ye olde days, the site actually had a custom theme
which used pictures of Dodd
, and Cassandra Roivas
(whose full-size image never got posted to a wiki and is thus unrecovered) for its buttons. While this was interesting and certainly unique to SOTF, it also had issues. A large number of members had no idea who these characters were meant to be. Of those who did, opinion was a bit split. It's really cool to have your character/work featured as one of the iconic faces of SOTF. That said, it doesn't feel great to not be featured. Since SOTF, in terms of both characters and handlers, is impossibly huge, far more would by necessity be excluded than included. Any sort of line of selection would likely be arbitrary (not really fun for anyone), voting-driven (turns what's already gonna to some extent risk feeling exclusionary into a popularity contest), or focused on "importance" to a version/the overall story (which doesn't feel good because one of our big ideas is that characters matter and are worthwhile whether they win or die on day two).
I dunno. I may be overthinking this, and I really, really love art of SOTF from our numerous incredibly talented handlers. I just also don't want something that should be a really positive celebration of the site to turn negative in any fashion.