After weeks of thinking, I've come with these possible routes:
"Cheap" endgame:
- Symphonium Meteor or Sennheiser IE600 + Moondrop S8 or 7th Acoustics Supernova
Standard endgame:
- 64audio u12t
- Elysian Diva
- 64audio u4s + 7th Acoustics Supernova
- Three of the 600-700 dollar sets, I'd also consider the Xenns UP and DUNU SA6 MKII as viable options
Money no subject:
Anole VX + Maestro SE
u12t + Anole VX
The big boy route is probably not going to happen, I'd rather choose cheap or standard for the sake of not going super homeless
My budget is going to be at least $1,500 USD or so