Need Recommendations for Hifi System Upgrade

Hello everyone!

This is my first time posting here so I hope I am in the right section…

Anyways I am looking for some help on what headphones I should get and an amp/dac to go with it as I fully upgrade into my first real ‘hi-fi’ level system. I will first go over what I have and my preferences, then I will go into my current thoughts on possible headphones and amps/dacs I think might be good.

My genres of music:

(Every genre depending on mood, but the following are kinda my top)

  • Classical (orchestral, piano, and more)
  • Electronic
  • Alternative
  • Rock
  • Some jazz

My Headphones/Gear/Preferences:
My first pair of headphones was the HE400i which I absolutely loved, it was a massive upgrade from cheap earbuds. Everything about it was great, but I especially loved the bass I could feel with it. Every headphone since then never really brought me that good bass feel, with quality.

I picked up a pair of Sony WH-1000XM3 for travel and ease of use. These are nice for the noise cancelling but definitely lacked in detail I wanted and got in my HE400i.

I upgraded to a DT1990 Pro and also picked up an HD6XX around the same time. This is when I bought my first amp - Jotunheim (v1, I think there is a new one now).
I really enjoyed the DT1990 and the amount of detail and clarity I got with it, absolutely blew me away, they were a big step above the HE400i. The only issues I had with the DT1990 were that sometimes I would get fatigued after listening for long periods of time with certain songs especially. Some songs I just cant listen to for very long on them.
The HD6XX became my backup headphone and one I used for alternative and songs with guitar or vocals. I really enjoy how these can make some songs sound and find them not fatiguing at all. The HD6XX did however have much less detail and clarity when compared to the DT1990 especially in the high range, but I find it is generally like that all over.

DT1990 vs HD6XX according to my ears:
So when I listen to a song with more instruments/more complicated parts mixed together I generally find the DT1990 was significantly better and I couldn’t even listen to it on the HD6XX as it was hard to understand what/where everything was and I couldn’t get lost in the music. The DT1990 however felt “thin or dry?” I think, when compared to the HD6XX in the midrange on some songs, especially with male vocals or guitars.

Now my questions:
I want to upgrade to a new system that will ideally be more of my endgame so price is not extremely important but I don’t want to throw around insane amounts of money. I would say I am looking at more of a range of $2000 - $4000+ (give or take) that I would be willing to spend on the headphones + dac/amp.

  1. What would the best system matching my preferences be where I can match each piece and maximize quality and enjoyment? (I listen to music for enjoyment, not for mastering or analyzing)

What I have looked at:
Some of the headphones that interested me initially were the Arya, LCD-X, and Empyrean. I know they are quite different but many reviews have been contradicting somewhat.
From my understanding Arya has a big soundstage, more of an airy feeling that would be great for classical music, and have very good detail retrieval. I have no idea how good the bass is on this headphone as no one seems to talk about it. I know the Arya also has good ‘sparkle’ or high range in general when compared to many headphones. But I think the Arya is more of an analytical type of headphone?
The LCD-X I have not done as much research on but it seems to be one of the leading headphones for bass. I don’t know how well this performs in everything else however. I have heard overall it is great and exceeds at electronic music. (I think this could be a good option considering I have the DT1990 for classical, but then I am not upgrading that experience).
The Empyrean is much pricier but seems to be aimed at enjoyment while keeping very good quality. I don’t really know how much better it is than the LCD-X and Arya or if it is about the same. The build is insane and comfortable and I like that since I use headphones A TON.

  1. Which of these would likely be a good pick according to my preferences? I would like some headphones that have some nicer bass but not if I have to sacrifice everything else.

  2. Additionally, are there any DAC/AMP combos that would be ideal for the headphone and somewhat within my price range? Should I upgrade the Jotunheim so that I get everything possible out of these headphones?

(I have looked at the A90/D90SE combo and A90/D70s combo, I think these could be good according to reviews. Not sure if they match any of the headphones or if there are better pairings with particular headphones)

Thank you for taking the time to read this, I apologize if I wrote too much/rambled a bit!

Edit: I am open to any recommendations, even if I didn’t list a particular headphone or amp/dac. I have looked at many others but didn’t want this to get too long.