Only if it messes with your daily life, personal relationships etc. I don't plan to keep more than two pairs of actual headphones (IEM don't matter) and one nice desk system around, but don't see anything wrong with having different hats to wear if you can afford it.
It’s of small consequence either way. But if you are keeping things you really don’t use, then that may merit reflection. I, personally, put a value on a lack of clutter, which I try to factor in.
I had seven headphones at one point with two dacs and 5 amps. It takes time to learn what you want and slowly you'll purge your gear from time to time. I've done three major purges over the past 6 years.
It's definitely a personal thing, I doubt that I could settle for one myself though I seem to be inching more toward that inclination. That being said, if you find yourself accumulating & selling frequently, you might want to take a look at that.
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