When Entercom was in its infancy, it expanded by acquiring unwanted FM stations when AM was still king. Some of its early stations ran classical, beautiful music, and Spanish-language programming because that was about all you could do with FM at the time.
I was in Houston when Entercom flipped KLEF (94.5) from classical in 1986. The new format: automated oldies. The River Oaks set flipped their wigs.
At least it got the Houston Chronicle to rediscover radio and actually write some articles about. The Post was much better about this sort of thing.
Entercom's best success, I think, was KITS, which started out as a Spanish-language station under different call letters. As a CHR station, it reportedly was no great shakes but when it went alternative, it blossomed. The current iteration of Live 105 reflects some of that, probably as much as is possible under present-day economic conditions for radio. Audacy's really boneheaded move with KITS comprised the years of "Dave".
I don't think Entercom's issue was not knowing what to do with classical. It had done it long enough to know that its legs had gone about as far as they could go with it as a commercial format.
Ingram made noises several times in the early 1990s about changing the format on KXTR. At one point there was talk of moving the format to AM, on KBEA. But I think if he had done that, there would have been adverse effects on his publications (Ingram's, The Independent), which were dependent upon the support of Kansas City's upper classes (Mrs. Bridge lived on!) and which seemed to be what he really cared about. Entercom actually made the change, stuffed KXTR into the AM expanded band, and changed 96.5 to an alternative format which did well for quite a few years.
If you want to say Entercom didn't have a clear vision for 102.1 in general, I would agree with that.
Another year, another format on 102.1. It felt more like, "let's dump this loser format on USC" even though it wasn't a loser format in the Bay Area. Entercom had preconceived notions rooted in standard program-director dogma, and the result was not pretty. And that was 15 years ago when financial pressures weren't what they are now.