Denver is full of these messes. Just about every signal serving every wide spot from Cheyenne (does that city even have any FM signals of its own now?) to south of Pueblo has tried to "move in" to Denver...usually with poor results. I haven't done the math, but 101.9 is probably not the only such station signal-wise, before and after.
WQKT's 60, by the way, touches downtown Akron and downtown Canton. It puts a strong, listenable signal into much of western Summit County and western Stark County. I caught it again in the western part of the area listening to see if it was carrying the Cavaliers' pre-season game (it was not), and it was very strong. Again, not so much east of downtown Akron, but there's plenty of population in the market west of downtown.
DE makes a very good point about car vs. home radios, though. The former WHK-FM/98.1 Canton put a listenable signal into car radios in much of Akron, but Clear Channel found out rather quickly that the station's stick east of Canton was a non-starter for in home/office listening. That led to the transmitter move to Hartville (northwest Stark County, closer to Akron), and the more recent move back into the heart of the Akron market from the old 96.5 site.
But we're kicking around two different points here. WKDD continued, even after the move to the 98.1 frequency, to try to market in Akron...and it was a miserable failure until the first transmitter move (and has even suffered from Hartville, forcing CC to move it back into Summit County, with the COL move to the Akron suburb of Munroe Falls).
Mr. Fybush has a couple of great examples around Ohio. WDFM's attempt to hit Ft. Wayne was ill-fated from the start. The signal is decently listenable (again, in cars, mostly) even without the booster, but CC would have to make more effort than a booster to sell this small town station in even the modestly-sized metro area of Northeast Indiana. (Heck, aren't there some CLOSER stations that have stuck to the home field? The station licensed to Hicksvillle, no?)
WREO has the same problem in Erie. They'd have to open up a sales office there, and make some effort to sell non-Ashtabula sponsors. Under Media One, they seem more content to mine the Lake County area east of Cleveland, which is economically much better off than both Ashtabula and Erie. They can sell Mentor and Painesville from Ashtabula, and with that signal.