I hate to trot out old tired examples I've used before, but it might illustrate your point. In 1987 KTVO at Kirksville MO built a 2000 footer midway between Kirksville and Quincy IL. The station was sold that same year. The next year, the tower fell during modifications. The new owners never bothered to rebuild, choosing to retreat to the original 1100 ft tower between Kirksville and Ottumwa.
In the process, a friend of mine lost his first TV job out of college, as KTVO didn't need a River Cities bureau when the shorter and further away 1100 footer could barely get a signal east to the river.
The new owners of KTVO at that time must have thought that sinking the insurance settlement they (hopefully) received back into a new tower wasn't a good investment, or the new owners were undercapitalized at the start, and the insurance settlement saved their shorts. It would be interesting to know how they arrived to that decision.
Moving on to a couple of current cases that I know: The Crown Point tower complex in Omaha has been home to four separate towers all in a row, each about 1200' for the original three TV affiliates, plus one used by several FMs. The city has grown up along the four towers, so it's landlocked today. It would seem that all of the stations would benefit by forming a tower cooperative, consolidating to one candelabra style tower directly adjacent to one of the existing towers, then dismantling the others and selling off the land.
Either the land doesn't hold enough value to make a shared tower worthwhile, all the different egos at the various ownership groups don't comfortably fit in the same room together, or the land DOES hold enough value to make a shared tower worthwhile, but the stations decide that it isn't worth the risk in case of a tower collapse during construction. Indeed, one of the stations at Crown Point, KETV, lost their tower in 2008 during modifications to install a combo VHF analog/UHF digital antenna.
Then there's the case of Saga's cluster of radio stations in Des Moines. Four FMs and two AMs, all at different sites. Two of the FMs are separated by 30 miles as they're 10.8 MHz apart. (93.3C1 and 104.1C0) So, those two aren't going to play nice together. A third station SE of Des Moines, 103.3C1, has to stay about 20 miles away from a separately owned C2 on 92.5, that 10.8 Mhz problem again.
In the 90s, Saga thought they had a solution. They proposed a single tower about 15 miles east of downtown for 93.3, 102.5 and 103.3. Alas, they couldn't get it through zoning. At least they tried.