I can't believe I missed this thread. I can't believe Chilly lives in St. Louis. Shit, now I have to be nice to her since I grew up there and visit twice a year.
St. Louis is definitely different from Cali. Let me address your points.
1. Just wait til summer. The temperature and humidity are often in lock step.
2. They're out there. Creve Coeur, Town & Country, Westport area, Central West End are a little more uppity areas.
3. You're not trying very hard. Listen to the Point (105.7), and follow Jeff & Thom around if they mention they'll be somewhere. Good time to be had by all.
5. Oh my freakin' God....don't write it off until you've been around a bit more. Tell me what you're looking for in a bar, and we'll find it for you. (See #3).
6. They are the "World Champion St. Louis Cardinals". Put that in your pipe and smoke it. Even a Yanks fan will appreciate how good the fans in STL are, and what a magnificent baseball (and sports) town it is.
7. Nelly is from the 314. Either way, just stick to 105.7 FM. They also have a great jazz radio station from SIUE at 88.7.
Sounds like you may be at Gentry's Landing, or maybe a pad in the old PET milk building (just south of the Millenium hotel). Walk down to Laclede's Landing and spend some time bar hopping....start at Morgan Street, or if you like it quieter, Hannegan's.
Laclede's Landing: Things to Do
Hope you like blues & jazz music played live. You lucky, lucky bastard.