Darkvoice 336se Vs Bottlehead Crack Headphone

Evening,
Pondering a new (desktop) headphone setup at the minute as I sort of miss the days where I could prop my feet up on my desk, throw on the cans and just chill without the outside world invading my listening (or sleeping which was usually the case in the evening sessions!).
Current and unused setup is AKG 550mk1 paired with an Aune T1 mk2 (with upgraded tube). I haven't used this in some while because compared to my hifi setup it's just completely sh*t in all aspects. My amp, cd player and speaker have a combined value of 4k+ RRP when new, so it's understandable that the 550 (€140) and a Chinese tube amp (€120) can't compete.
I really don't like the AKG 550, so deffo not looking to replace with newer versions. As a person who wears glasses they never sealed well on my head, so the low end was really quite sub par. They're not very comfy either, so when I did use them for hours my head would hurt at the end, unless I wore them loose enough to where they would slide off.
The Aune was a good introduction to headphone amps and tune rolling, but as I've graduated into better equipment I'm looking to improve this with a better tube amp (I like tube rolling as you can change the sound for cheap).
I'm not rolling in cash at the min, so will be buying in bits with a budget around the 1k mark.
So, on the list of amps I have:
Darkvoice 336se tube amp
Bottlehead Crack
Schit stack (of some description)
Ideally I'd like an RME ADI-2, but it's costly and maybe a bit too much for primarily Spotify. Will move onto hi-res once we get fiber to the house (a year away at least). Our current ADSL connection can't handle streaming hi-res.
anything else to consider? Doesn't have to be tube based.
As for cans, all I can think of at a decent budget level is the Senn 650. Anything else to consider here? I primarily listen to jazz, female vocalists and a touch of electronic music/hip-hop.
I'm open to used as long as the availability is there.