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I have not owned a ton of headphones, but have heard a few different types.Owned or own now:Westone iems (own now)Sennheiser Momentums (own now)Grado SR80i - stock and then very moddedAlessandro MS1Beyerdynamic DT880Panasonic noise cancellingShure se215 iemsKoss PortaproHave heard:Shure SRH-1440 Sennheiser HD600Hifiman HE400 I will be following the used market with interest in the coming months. The Matrix will drive headphones up to 300ohm, so it leaves a lot of choices.I enjoy the Momentums just fine for times I want/need a closed back phone.With a dedicated headphone setup being put in place in the living room (gear will be out of sight) I will likely want to also have a set of open back phones for certain days too.Won't want to spend more than USD$250.
At that price, the Beyer Custom One might deserve a spot on the shortlist, although I can hardly argue with your choice of the Momentum.
Generally tube amps are more suited for higher impedance headphones, unless we're talking hybrid amps, which are usually good for a wide variety of impedances.Made me think about allocating resources for a collection of very good headphones vs one really great one.
Depends where you are in relation to the law of diminishing returns is how I look at it. If that one headphone is truly great, and sounds truly great on almost all the source material you will be putting through it, that's one thing, but in most cases, a (let's say) $1.5K headphone is not ""twice as good" as a (let's say) $750 headphone (obviously there are many variables here). I kind of like the flexibility of choice that headphones make easy compared to speakers.... Pick something off the "rack"... Would you want to go to the same restaurant every night, even if it was a four star restaurant?