I’ve lost count, but I have probably owned around 30 headphones and countless DAC/AMPs. I capped out at $1.5k for individual headphones and roughly the same for the DAC/AMPs.

At the end of it all, I realized I was never going to be happy with one. I got rid of everything except AirPods Pro 2s and the AirPods Max. I barely use the Max, but the Pros are excellent. I found that in the end, I personally do not miss the higher SQ and it just ends up being a giant money pit.

Speakers (if you have the space/place for it) are the answer in my case. I’ve owned a lot of speakers as well, with KEF LS50Ws being the peak. I ended up settling with Vanatoo T0 with a Monolith THX 8” sub, and it’s amazing for desktop use. I found that I enjoyed this more than any headphone I’ve used.