I often find these sorts of discussions irrelevant, simply because it tends not to be a discussion at all. Party A has an opinion, party B, another, and neither, in most cases, are ever willing to budge, or does try to seek and understand the viewpoint of the other (one needn't accept, to understand). Where lies the point then?
To say that all the more expensive equipment wouldn't sound better than their cheaper counterpart - although there is always an exception to this, as there is to just about everything in life - would be invalid statement.
Therefore, to say a person can extract more enjoyment from something that is cheaper than something that is more expensive - regardless of the actual quality of the utility it provides - would be more accurate.
My current setup sounds 10 times better than just my ipod, and them mediocre Bose headphones I used to have, but the truth is, I enjoyed the music more there than I do now here. But I can still acknowledge, my current setup is 10 times better than its former equivalent - 10 times, not a 100, as the drastic price difference between the two should, as we would like it to, mark.
I'm still seeking for my, as I'd like to call it, headmate.
(etymology: derived from 'soulmate')