Ardbeg, where in Chicago do you live? I grew up in Park Ridge and lived in Lincoln Park for a bit before moving away.I would get two systems - one for work and one for home. One tube, one solid state. The tube amp should offer some tube rolling options so you can bend it slightly wet or dry, etc. to taste. I'd recommend tube amps with tube rectification (more sonic tuning options to again bend to taste w/o having to buy a net new amp as your tastes subtly change over time). Relo the headphones between the two locations depending on mood (and because most TOTL headphones come with some type of carry case to faciltate transportability). Regarding the headphones, given your genre preferences, yes, the 1266 is an option but (as a former owner), I find their sound signature a bit niche if you are going for widest use cases. There are other very, very competent alternatives also with excellent bass and less sonic quirks -- Final D8K or D8Kpro, T+A Sol P, a gently used LCD-4 (the last one is quirky but not as quirky as a 1266). Susvaras live up to the hype (but do not buy new and especially not at full retail price). I owned the Sus, they gave me a headache but that isn't the headphone's fault but instead my individual frequency response sensitivities.
I looked at those HPs and the Final 8000 sounds very interesting. I think I have a list of TC, Utopia, and Caldera to try and maybe should try the Finals too. What would the 8000s niche be vs. those others. And vs. the Sus, from what I can gather they are also resolving but have more low-end quantity (not saying they are better than the Sus). Any other major differences?