This is kind of what i am doing right now. I made the mistake of creating a spreadsheet in order to find out how much money i have invested in this hobby, the total was CAD$8200 (US$6300) which is something i was not expecting, lol.
I have decided to sell everything to bring the investment to something i find to be reasonable, i am only keeping my DAC which is a Modius, my Burson Soloist, the HE6se v2 and the Kennerton GH50.
Everything else is listed:
Dunu Zen
Mangird Tea
Fostex Ebony
Audeze LCD-X 2021
LSA HP-2
The HE6 is so good i am ok with selling everything else, if this was 1 year ago before i got the Soloist + HE6 i would never think of keeping only 1 or 2 sets, if money really was a problem i would also sell the Kennerton and keep only the HE6, fortunately i can afford to keep 2 sets though. The Kennerton is unique enough to justify keeping it