Thanks @soix for the thoughts and ideas. They're right on I think. I just bought a pair of HifiMan Sundara phones to try out, and since they're middle of the road I can start there and determine if they are "good enough" or if I want to try something upwards from there.
I'm also going to start building the DAC/Amp side of things and I think I'm starting to understand it...
I'm also going to start building the DAC/Amp side of things and I think I'm starting to understand it...