Any idea which headphones I’d like?

@soix I’ve generally leaned towards “warm.”  I don’t prefer bass heavy vs. detail.  I’d say the one thing I’ve always really liked is a large soundstage.  I prefer a warmer midrange, with accurate bass vs analytical with some bass bloat.  I do not like mushy, I sold all my McIntosh gear because I felt it sounded “mushy.”  

I’ve always really liked Dynaudio speakers.  I hear a neutrality in them, that I didn’t really hear anywhere, until I heard the Harbeth’s.  I just prefer that the gear not color anything, that’s all.  The Pass Labs + Harbeth was a winning combo to my ears.  

@james633 Thank you for the info!  Ahhhh, the beautiful last 5% that makes us spend our discretionary income…and sometimes then some on audio gear!  

Don’t get me wrong, I really did like the sound.  But I have the opportunity to focus on that last 5%.

Per the Sennheisers, I’ve read that they really need tubes and become almost magical with the Western Electric 300B tubes.  And I actually may have listened to a set, being driven by one of the McIntosh HA’s.  I didn’t come away thinking anything other than, “jeesh, McIntosh is ripping people off with this thing.”  

I’ve read some very positive reviews on them, out of curiosity, what is that you do not like about them?  

So, Clear MG’s over Utopia’s?

@master92, do you use them for Mastering?  

With your budget, you should consider the Focal Utopia.  I have the Focal Elex from Massdrop and they will give you the kind of sound signature you're looking for.  The Utopia will give you more of what the Elex does.  I listened to some Utopias, and they are beguiling.  I have Harbeth Super HL5 Plus and P3ESR, and of the dozen headphones I have, I would say that Focal headphones come closest to the Harbeth sound.

I wouldn't dismiss Sennheiser.  I have the HD800 and like them very much.  The HD800s is supposed to have tamed some of the "brightness" that some complain about with the HD800.  I have not heard the HD800s.  The $200 Massdrop Sennheiser 6XX are probably my favorite headphones, but more for reasons of comfort.

I have not gone up the Hifiman line, but I have the HE560.  They have a similar, but more neutral sound signature than Audeze.  My Audeze headphones are more detailed, and they do more than just bass well.  The LCD-4 are pretty amazing and have a great midrange.

Lastly, the Sony MDR-Z1R deserve consideration.  They sound very similar to the LCD-4, at about half the price and are a lot more comfortable.  The LCD-4 is probably the heaviest set of headphones I own.

For amplification, I have a Simaudio 430HA.  If you do get the Hifiman headphones, consider their EF-6 amp.  It's discontinued, but you might be able to find one at a reasonable price.  Sony's headphone amp is really good also.

Forget about "soundstaging".  You have two speakers on the side of your head.  You simply can't get the same kind of imaging or soundstage that you get with speakers.  Some headphones will do a better job than others of not making this apparent, but headphones by their nature will give you a completely different listening experience than speakers.  I rarely use my headphones anymore, in large part because my two channel systems have gotten so good.  

“ is that a Woo Audio tube setup, by chance?”

Yes, my system has a Woo WA5-LE. I have had several Woo amps WA6… and WA6se. Each in turn sounded better and had more power. I wanted to go a couple steps further. And it was well worth it. The WA5 has enormous power and beautiful midrange bloom. They are just magical to listen to… but not in any artificial way… incredibly musical. I get hooked on listening because I am enjoying it so much. It took control of all of my headphones and pretty much told them it was in charge. So, the peculiarities of the headphone disappeared and they all started sounding like the electronics I had chosen.

For the tubes. After receiving the amp I was enchanted and loved the power and realism it brought to all my headphones. So I got the upgraded tubes that Woo recommended.. the Takatsuki 300B. I upgraded the others as well. The Takatsuki are glorious.

The change in my headphone system was so profound and fundamental that it caused my to completely revamp my main system… going to all ARC tubed gear. I think doubling the investment in that system. While all of this was expensive, my systems sound much better than I ever thought they could.

https://systems.audiogon.com/users/ghdprentice