Annapolis is nice, with a lot of history. However, as part of the Baltimore-DC area, the traffic can be awful. The bridge crossing the Chesapeake right next to Annapolis is the only crossing for some distance and traffic can just stop for long periods of time.

My parents live not too far from Cape Girardeau. You'll find most of your typical chain stores and restaurants there. It is also a college town. However, it does have a very rural feel to it. If your used to big city life, you won't find it here.

I can't comment on the other two places.