For a long time, Atlanta was one of the most profitable radio markets in the US because it had a really small number of stations for the size market it was. That's because the original table of frequency assignments drawn up by the FCC was created before the sunbelt started to boom.
The south also has something we don't have much of here, full "Class C" FM's. They are 100kW on towers as high as 1,300 feet and cover huge areas. We don't have them in the northeast because large markets are closer together, and we have to protect Canada. By comparison, a lot of New York City FM's are 10kW on top of the Empire State Building.
But if you could get one of these big blowtorches licensed to a small town, you could move the tower halfway to the big market and put a city-grade signal over both, and thus you fulfill your technical requirement for local service and can sell in the big market. What a concept.
Again, I'll use Orlando as an example since I know it. You have stations in that market (and some of these are the top-rated stations) licensed to cities such as Daytona Beach, Mt. Dora, Deland, Cocoa Beach and Titusville... almost a 50-mile radius.
The most aggressive move-ins here involved 105.9 and 106.7. Clear Channel somehow convinced WAMO to give up 105.9 in exchange for 106.7 and some cash. 106.7 had been a very troubled signal during its Beaver Falls days, and Sheridan had to eventually buy 107.1 and move it further away from the city to move 106.7 in to Wexford. (You can never get closer to first-adjacent channels, those are ones that are .2 away on the dial... there is some room to play with second-adjacent, which is a .4 space.).
It took many years to get 104.7's tower into the city from New Kensington, where the original site was located with WKPA. And of course Froggy used to be WESA.
For a long time WLSW was rumored to be upgrading and moving in closer as well, but there was some issue with Ohio stations and maybe selling the station to Cumulus, and that eventually fell through.
There aren't many other opportunities I can see in Pittsburgh to bring anything in from further away, although the one I can think of is WLER on 97.7. It would be tricky between BOB and Froggy, although now Keymarket has a repeater in Monroeville on 97.5 for that Christian format they are doing.
92.1 in New Castle could also likely be moved in, although you'd have to get Pitt's 10-watter off that frequency. Cranberry would make a great city of license.