IMOS is the shit. Check out the Delmar Loop http://www.ucityloop.com/, soulard http://www.soulard.org/businesses.php, italian restaurants on the Hill http://www.thehillstl.com/,
GO TO A CARDS GAME, and there are tons of gritty grimey places to paint.
edit. no one bumps nelly here and juggalos are faggots. crack heads are a common sight.