You and Rusty did not address Stanley's question. He is the WECK listener who complained. A station manager may not tell a listener outright "You listen too much", but that's the gist. The average person may only listen an hour or less a day.
There are different levels of listening. Some people only listen for one or two short moments in the day, such as a 20 minute commute or when getting breakfast or the like. Some listen all day. Others only listen a few times a week. Stations program for the medium and heavy listeners, but the mediums are what drives stations. So rotations are based on a combination of how many songs in total tested well and how we can schedule songs so they play in different dayparts and hours before playing again in the same hour.
Each format has different mechanics, so there is no one answer to your question; that's why you don't get an "answer" but a "situational analysis". The listener, if given any explanation, will be told that most listeners want to hear the songs that often, and "we're sorry it's too often for you".
That said, in my years in radio and at a lot of high repetition (every 90 minutes at some) formats, I've never really been told "you play the songs too often". The closest that comes to that is when a listener complains about hearing songs they don't like too often. You generally can't play favorite songs too often unless you repeat one back to back, over and over.
I know of a station that was classic hits / oldies about 15 years ago in a very big market. They would occasionally take one of the high research songs and play it twice in a row. They called it something like "double barrel" and it occurred at random and they talked it up and had a special sweeper. The jocks said that when they did appearances, it was frequently mentioned as an "I love when you play one of my favorite songs over again!"
You get negatives when repeated songs are not liked by some / all listeners.
Of course, Radio is a business. Just playing the hits does not guarantee success. I can find many examples of failed formats. They have recycled the same ideas for years. They also make futile attempts to tweak stations (JOY to MIX to BREEZE). Playing it safe isn't always a winning formula...
But if you try to count the number of "new" formats in the last 60 years, you barely get into double digits. Everything is a progression, refinement or modification of something already done. Example: AC was known in the early 70's as "chicken rock" and it was just a modification of Top 40 without the hard stuff and the teen stuff.
In every field, from laundry detergents to frozen foods, there are new product launches that fail. About 60% or so of all new consumer products do not make it through the first year or two. And those that are launched went through extensive research.
If it were possible to research success perfectly, every song released would be a hit and there would be no stiffs. There is a high degree of uncertainty in any new product launch, whether it is a song, an electronic device, home goods or consumer products... or formats.