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My husband suffers from tinnitus, which is ringing in the ears. He blares the speakers to try to overcome the ringing. Are there any quality (as well as comfortable) headphones that might simulate surround-sound? And is it possible to run the headphone cable 12 feet without affecting the sound quality?
I can't really comment on the other things, but the cord length is negligible. My Sony's have about 30 feet built in so I'm sure it isn't a problem. You have to start talking 1000's of feet before impedance effects cable length enough to matter. Since we aren't really talking hi-z and low-z instrument cables, there is nothing to worry about.
Tinnitus can be caused by ear damage and blaring headphones directly into his ears will make the problem even worse, so I wouldn't advise it. Maybe he should look into assistive devices if it's that bad.