The average person listens to radio an hour or two a day, not 6 hours in a row. And the songs most listeners "score" high get played often because that is what listeners want. Stations that have tried to compete with bigger libraries have almost uniformly failed.
As to older listeners hearing those same songs over and over, I'll mention one interview I conducted for an "oldies" station in DC many years ago. In discussing the songs she enjoyed, and digging about "why?" the answer came out: she was a file clerk for a government agency and did the same thing she had been doing for nearly 30 years in the third basement archive rooms. The songs from "when I was in school and college bring back the only fun years in my life and they make me feel good!"
Yet those jocks did not pick the new records. The PD and MD did, and introduced 3 or 4 new ones a week that had been carefully picked as "hitbound" or "future hits". Even then, if you look at stations charts from the 60's, 75% of the "future hits" were actually stiffs.
And zero ratings. And billings around $25,000 a month while WDVE bills about $1,000,000 a month.
You like comparing with WDVE. So the 12 stations and translators those folks own all together bill less than WDVE bills in two months.
While it is nice to find small operators of marginal stations who are able to sustain stations with deep niche programming, the larger audiences are elsewhere.
I absolutely understand that WDVE bills far higher than WKVE does. No question there.
I actually think that makes what KVE does that much more special. They know that they aren't going to attract an audience the size of WDVE. Appealing to the masses doesn't always make a 'good' product. I can think of many products aimed at the masses that are... watered down, minimalist, and devoid of any quality and creativity. And a lot of those products likely bring in a lot more revenue than their handmade counterparts, etc.
This world isn't all about making the most money and having the highest billing for everyone. Some people prioritize that. Others prioritize other things. It is obvious that making the most money possible is not the primary driver for the Stevens. Otherwise, they would not program their stations the way that they do. Rather, I suspect their goal is to provide incredibly enjoyable programming while making a decent living. While I do not know what they make once all expenses are paid, they certainly succeed at the first part in spades.
I wasn't trying to say that every radio station should have a giant library. I get that that's not the way to maximize billing. But as a listener, I really appreciate when a station goes against the grain and airs a large library. I equate it to the work of a fine woodworker. Are they going to make as much as Ikea? No way. Not even close. But they are going to provide a higher quality offering that will likely impact their customers lives far more than Ikea (and yes, they will obviously have fewer customers than Ikea).
Oh, and I picked the jocks I did in my example above for a good reason. Those guys were not bound by a PD who picked what they spun. They were not spinning the "hits" that KQV, Pittsburgh's Top-40 giant was spinning. Most of them also DJ'd dances around the area and had their own unique records. They'd get them from the cutout racks and back rooms of record stores. Heck, Mad Mike would literally scratch out the labels on his 45s so that
nobody else knew what he was playing. These DJs were insanely popular and I get calls on my radio show regularly from people asking why I focus on the KQV surveys because "Porky" or "Mad Mike" or "Terry Lee" was who they remember most from their childhood. KQV had ABC's backing. While it is remembered in Pittsburgh, the aforementioned jocks at small local outlets are the ones most discussed today with the exception of literally one, and that's because Clark Race was on the 50,000 watt blowtorch KDKA.