A/V Receivers and which high-end headphones "if any" will sound best for it's purpose?

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Thank you. You are exactly correct. I’m going to try using what I do at work, PROCESS to try and help. @Cyan69, and others, let’s try to play along.

So this is the 5 point process from work (Edward Jones)

  1. Where am I Today?
  2. Where do I want to be?
  3. Can I get there?
  4. How do I get there?
  5. How do I stay on track?

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  1. Where you are today

You are using electronics that you like, but from what I understand, you feel something is lacking. Several here that know the receiver you use have pointed out the weakness, specifically, of the headphone output on that equipment.

We have asked you about your software, and you have not responded to that. You have described a process of downloading files to a flash drive for your music. We do not know where you get the files, or what quality, but if you use DSD, some of us suspect they are movie or DVD related as this is where most DSD is found.
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@NickZ, @bpcarb, @PaisleyUnderground, @Tchoupitoulas, others please jump in, referencing the process step. @Cyan69, please try to address this clearly and concisely

  1. Where do you want to be?
    This is the point that @NickZ says there is a disconnect. You know that headphones make the MOST difference, and you have some well-regarded headphones that you like. You have a budget in mind. You already understand that cables should be good quality but the last area in which to sink big bucks. You have defined Rock as a preference,
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    We need a timeframe. I suggest not being hasty. We know that you will want to try at least one or two other headphones,

  2. Can I get there?
    This is possibly the easiest point. Yes, with $2000 almost certainly. But as the White Rabbit pointed out to Alice, “If you don’t care where you are going, then any road will do.”.

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  3. How do I get there?
    Several of us have suggested that you may need to swap out some pieces in order to find out what’s not working. As far as I can see, the pieces may be:

    • Your Software
    • Your Receiver’s headphone output
    • Your headphones

We don’t know about your software.

Several of us have suggested $200-400 in DAC and AMP. This is the process of swapping out your headphone jack, which several regard as problematical. It is within your budget, and if it’s not the right first step, you can always resell the equipment,

Your headphones. We don’t know exactly what you think you are missing (steps 1 and 2). Headphones have the potential to be the most expensive part of your budget. And if we are not certain about how they are being driven, you can’t make a rational decision about which ones to try. That’s one reason that I suggest taking your time, and seeing about the issue of driving the headphones properly.

  1. How do I stay on track?
    Keep asking questions. Try to eat the elephant one bite at a time. Ask one or two concise, burning questions, perhaps using the crutch of bullet points to focus us on your concern.

Hope this helps!

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