[Mkubota1]

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Artists refusing to come to my house and perform for me personally

That, and the restraining orders keeping me away from their homes or studios. 

 
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The recording/source.
Not the equipment, I have lived for 10 years with budget Sony MDR-CD270 headphones and never felt I missed something, there only was the annoyance of a poor recorded CD at times.

x10.  They keep coming out with new technologies (CD, better DACs, higher bit rates...) but none of that compares to a decent recording from the start.
 
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I'd have to say that Audio Engineers are the biggest obstacle.
 
The crap that passes for engineering so that music will sound "good" on crap gear makes it tough for me to enjoy what I know darn good and well could have been a great recording is what keeps me from AN.

Ties in with the previous post.  I really hate having to base my musical taste on the technical merits of a recording, but that is often what it comes down to.