Ya kinda get the feeling that the seeds of this mess were sown back when the FCC loosened the ownership restrictions?
No, I trace it to Docket 80-90 that overpopulated the dial in every small and medium market and made profitability tough in most bigger markets due to move-ins and upgrades. Docket 80-90 forced the FCC to loosen ownership rules to make up for their mistake.
Before dereg, the stations were in many cases owned by the person or company that originally put them on the air. There was very little debt service and the people who ran them were well experience in broadcasting.
That is not true with rare exceptions. The big independent companies of that era expanded by building up to 7 AMs and , later, 7 additional FMs. When they were at the limits, they sold the smaller ones.
In 1940, we had under 1000 stations in the US. Now, we have over 15,000.
By the 50's, many of the original owners were out of the business. Some moved to TV, others got out of radio. The limitations of just 7 stations of any type kept larger investors out and the feeling that "radio was over" in the 50's got many early owners to cash in. For example, in the later 50's The Cleveland Plain Dealer felt that radio was dangerously decrepit and they sold WHK to Kluge.
George Storer started with an AM in Toledo. He added things like Wheeling and Fairmount in West Virginia. When he moved upwards to San Antonio, Philly and Detroit and Cleveland, Fairmount was sold. And then Wheeling went away to get Miami and then smaller ones were sold to get KGBS and WHN. George Storer never put one on the air originally.
The same goes for the big names in radio's rebirth in the 50's and 60's with companies like Eaton's United Broadcasting (Aaaaaaarrrrrgggghhhh!), Rollins, Storz, McLendon, Air trails, Gene Autrey Station, Balaban, Bartell, Crowell Collier, Vic Dieham, Fetzer, Good Neighbor, Forward, Hearst, Kaiser, McClatchy, Meridith, Metromedia (Metropolitan), Peoples (Nationwide) Palmer, Plough, Rahall, Rau, Ridder, RKO General, Dee Rivers, Seaton, Starr (Burden), Susquehanna, Taft, Time, Transcontinent, triangle, Westinghouse and lots of others.
Just look at the group ownership section in the 1960 Broadcasting Yearbook here:
https://worldradiohistory.com/Archive-BC-YB/1960/BC-YB-1960.pdf
Each of these companies, big or small used debt to expand to additional markets or to trade up when they had the legal limit of stations. Some were good broadcasters, others were not so good.
The FCC actualy had some teeth and fines were pretty rare. Stations hardly ever went dark
There were only 600 FMs in 1960 and the number of AMs was about 35% less than today. Daytime AMs could make money, and markets had not outgrown the signals. Today there are 3 times as many stations, and ad budgets are not sliced as thin due to new media.
The FCC did revoke licenses, and competing applications were more common at renewal time. As to "teeth" the FCC mostly regulated technical matters and equipment was far less stable and reliable. We have outgrown that for the most part.
Then, after dereg the wall street sharks moved in. They paid crazy multiples for broadcast properties and had astrinomical debt service. Bankruptcies skyrocketed. Diversity of ownership and programing vanished and properites started going dark.
In real dollars, radio bills about 35% of what it did in 2000, with many more stations and new media competition. The signals that don't fully cover a market are failing. AM is of no interest due to quality of audio outside of seniors. Big Box stores killed local revenue in Lake City, FL or Charlevoix, MI or Prescott, AZ.
The FCC allowed consolidation because by 1995 over half of all US radio stations were losing money. And the companies that wanted to stay in radio all wanted to buy lots more stations, so they overpaid... just before the Internet hit us all in the face!
Programming diversity actually expanded greatly under consolidation; if you owned 5 FMs in a market, they all could not be CHR or AC. So group owners might each have 5 stations in the top 20, but some of them had formats that were 13th or 16th or whatever, but combined they made great packages. So markets ended up with lots more different formats than ever before because owners could be happy with one or two in the top 5, one or two in the next tier and a couple below #10 in share.
When I was a kid in Cleveland in the late 50's, we had 3 Top 40's, 3 MOR stations and two Black stations out of 8 viable stations. Now, there are about 24 different formats on 39 stations licensed to the market.