Wow, I came back from a long week of work to see all these great responses! I wish I could quote all of you, but i feel like it would just make this post way longer than it needs to be.
Reading through everyone's post, I decided that I need to experiment a little to determine what I like in order to develop a upgrade path (or perhaps just be content with what I own). I'm going to head to my local guitar store which recently opened up to give some different headphones a demo. Hopefully as the situation improves here in the US (not in the foreseeable future), I'll try and find a local meet up. As for trying other cords/dacs/amps, I'll have to play around with my budget a bit and see if I can find some used ones to try.
Thank you all for your help! If I run into more questions, I will post them here. You guys are awesome.
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