Sennheiser HD800(the original).Known for a slightly hot top end with very good everything else.
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Listening to headphones at low volume is fine, it’s when you dial up the volume that it becomes a problem. I also recommend open head phones instead of in ear headphones if possible. The Sennheiser HD800/s are excellent. Others, that I’ve enjoyed at the Grado PS500e, GH1 and GS1000e. Grado headphones are just very natural and musical and they emphasize the upper range so it helps people like us with some hearing lost. :) The top of end Grado PS2000e is fantastic but out of your price range. Btw, If you look on www.massdrop.com they have some great deals on headphones. They recently or still have the Massdrop Sennheiser HD6xx (same as the HD600) at $250 which is a bargain. This has been my goto headphone when I can’t listen to the stereo late at night. One the best value in audio if you ask me. Right now, they have the Massdrop Focal Elex which seem very nice. Massdrop keeps rotating in new headphones so keep your eyes on the site. Good luck!
thanks i was just reading about the 660., really more in my price range. Cant do the HD 800 right now. I do want get a headphone amp beyond my dragonfly. I've read over and over that that really helps. I have Focal power monitors so Im interested in their phones. I heard their base model towers and they are really good.
Shure SE846 are the best IEM period. Etymotic ER4 were good once (like 20 years ago) but have long been superseded. Headphones will be easiest for audibility as there is no room reflection/reverb in the sound and these IEMs eliminate all background sound by 37dB making critical listening much easier.
For computer speakers Genelec active 8020 would be ideal they are not true reference like ATC but have a pleasing coloration with a small tilt up in the treble which should suit your hearing.
If you are doing recording projects then ATC is best as they go very loud without any change in the sound balance and little to no compression. Honestly though, if your hearing is shot (my sympathies as this must be so frustrating) then you probably should hire others to mix and master your recording projects....
FYI Clarity in sound production is a problem with a lot of modern bass heavy speakers and headphones. Resonant bass will mask midrange ruining clarity. With ER4 you have very little bass so you are on the right track. For speakers ATC are very tight. Totem tend to be mildly bass boomy and are pretty good compared to most hifi bass heavy speakers.
OP if your considering headphones have a look at the new generation of Planar Magnetic cans by HiFiMan & Audeze...You basically get a speaker like Magnapan in a headphone easy to drive...They are know for highly accurate sound and have beautifully extended treble response...Also have a look at Grado and AKG,both known to be lit up on the top end...