Andy, you bring up a good point that a friend and I have been making for years now. In the age of smart speakers, a unique branding should be more important than ever. Just a few examples,
1. If someone says to their device of choice "Play 99.5 The Wolf," are they going to get Dallas when they want Portland?
2. Same applies to Z100. If they say "Play Z100," they're likely to get New York, when the wanted station may be Portland or even Missoula, though the Missoula station is a Townsquare station, meaning that you actually have to enable the skill.
3. The same friend I mentioned above, who lives in upstate New York, has both Family Life skills on her Echo. One is the local network heard across New York and Pennsylvania, the other is the similarly named and similarly formatted network based in Arizona. I can't remember which is which, but one is Family Life Ministries and the other is Family Life Communications. Wouldn't it be a benefit to both brands if they either merged or one rebranded to something a bit more unique?
4. I was going to leave it at the Family Life example, but then I remembered there are actually documented cases of listener confusion. The most notable example in commercial radio is the confusion of listeners between WBEB in Philadelphia and WBWB in Providence, both at the time using the name B101. Another good example is a public station in CA rebranding as KVPR last year because their former name, Valley Public Radio, had the same initials as Vermont Public Radio, causing listeners to send their donations intended for the local station to Vermont instead.
I could go on and on about this, but I'll leave it there.