@801evan
Hello, I read your long post and all I can say is you are still under the spell that all these gadgets affect the digital bits.
Learn from.those who have been down this road;
It's all about RF noise. And ALL your gadgets just alter the amount or character of the RF noise. NONE do anything to change the bits.
So when you describe colorful changes to the sound you are really saying is; my Hugo2 is a frikkin scientific instrument to detect analog RF noise ...and I can discern that each change I make to my chain alters the sound.
I am writing this with hope that you may consider that all these devices and software or source changes are doing nothing but changing how much, how little or at what frequency RF noise is riding on your usb cable. It's not jitter or imperfect eye-patterns you are hearing. Certainly it's not bit errors.
Try an optical (TOSLINK) connection to hugo2, remove all other inputs(metal wires), go on battery. I am sure you will be floored (as I was) when you hear your music unaffected by RF.