I couldn't give you any advice about where to cosplay coz our place in Illinois(well, im in the Philippines right now) w/c is less than an hour away from St. Louis is light years away from where you are...I think St. Louis houses a bunch of cons but i'm still not sure, it's a busy metropolis so the probability of a con being held there is quite high...
There was this book con that i managed to attend by luck during a trip to San Antonio. It look liked a con/flea market tho, i hauled mangas, a couple of D&D books and other miscellaneous stuff.
I'm currently in the Philippines, and i've been attending lots of cons here for the past couple of months. As far as con experiences go, i'm like what you said, a swag collector. That's my only purpose why i attend cons. I don't mean to bash our local cons here...but based on what i've seen, it's not really excellent...But still pretty okay, even though it has boring tendencies...
Disturbing occurance? Good cosplaying events due to the really bad cosplayers....heh. Although not all cosplayers here are THAT bad, some are. That takes us to the advising part:
Who to cosplay? Beard and glasses, there are lots of characters like that but i dunno if your exact look matches theirs. Just pick a character that you can portray visually and make sure you act like it. I've seen cosplayers here that cosplayed characters that doesn't even match their overall look...think of a small and chubby Nicholas Wolfwood, or a pot bellied Joe Higashi..i've seen both.
I've also seen people that looked the part but was too shy to act like it. I've seen a constipated Haruhi and a bunch of Rock Lees that moves no better than my 90 year old grandma. Y'know what i mean right?
However, there are cosplayers that deliberately makes goofy versions of the character. Like a 6-foot male cosplaying Sailor MOon, that was positively funny and and exception to the ones i've mentioned above...
Good luck on your future cosplays. Do your thing and steal the show, on a positive note, that is.
