Ideally you can have a headphone that excel at something better than others for certain genres. For example, 2 headphones I frequently use are the ZMF Atrium and ZMF Verite Closed. When I want a warm bassy head headphone with amazing soundstage I’ll go for the Atrium. When I want better imaging and a more neutral sound that still is very lush I’ll go for the Verite.
In my collection I also have the Focal Clear MG, Arya V2, and a Modhouse argon.
That said, I like to keep the clears because I find that music that wasn’t recorded well can still sound great on it. The Arya V2 is when I want some spicey treble and it better for certain genres.
That said there has been plenty I have sold/traded. And largely it’s because I found something better in the models I listed above. So with that said it depends on use case. For me I love the hobby and like having options, every once and awhile I will downsize to try new things.
Eventually you realize you have the best of what you’re currently into. Warm headphones and soundstage have always been my thing, but recently I’ve come to value imaging more because of how holographic a soundscape can be at times. I’ve come to learn that, that comes at the cost of the warm signature/bass typically. (ZMF atrium stock pad vs caldera superferoated proved this to me).
The answer is probably yes, but also everyone has a preference and not one size fits all