While I'm far removed from the sales aspect of radio, I do know of two examples where the non-protected contour produces/produced significant revenue. The former WJCP 92.7 Austin,IN had studios in North Vernon,IN which, at the time, was outside of the protected 60db circle (they have since doubled power & North Vernon is now just inside the 60db contour). The lion's share of that station's billing came from North Vernon. The other example is a non-com, WIKL 90.5 Greencastle,IN. Their 60db contour just scrapes the I-465 circle around Indy, yet when K-LOVE has their pledge drives, this station is consistently among the first to reach the local goal. This station is directional and doesn't reach any other significant population.
While these two examples don't provide rock solid proof that areas outside the protected contour can be sold, it seems likely that money does change hands outside of the protected areas.
Unrelated, but since you (w9wi) are in TV engineering, I went past the WSM tower on I-65 Thursday & was again reminded that there is a TV antenna at the top. Is that still in use? If not, what's the history behind it?