I grew up in Creve Coeur. I went to private schools, but that is Parkway School District. It's a nice area, but a little on the pricey side. My parents could not afford their house now.
We are moving back and we chose to move to Wildwood. We'll be working farther out though...St. Charles area most likely, possibly Eureka or around there. I love Wildwood...we have a 2 acre lot, trees, wildlife, but we're still relatively close to the major areas of Chesterfield and the new Wildwood Town Center. It would not be the most convenient for a downtown commute though.
My husband would not go for some of the other places I like. As far as older houses with character, I love the central west end, webster groves, kirkwood. I also love Clayton.
For school districts...Rockwood, Clayton, Lindbergh, Ladue, Parkway...I'm not up on the others.
People in St. Louis also think direction. North, South, and West County, central county. I would choose west or central followed by south. I would personally not choose north, but there are nice areas there too I'm sure.
Then you have St. Charles, a bit of a tough commute and very suburban, but growing fast. You also have the suburbs on the east side...we have a few friends in Edwardsville and they love it.
I think the city has some great areas with cool housing, but horrible schools. So the choice to live in the city has to consider what your schooling choice will be. If it's home or private, you can find some great spots. If it's public, you may not want to consider it.