Knowing me, Id realize and appreciate the upgrade more going through the first aforementioned way, and understand audio a lot more whereas jumping into say, those beyer dynamics, from where I am now, all I could say is they sound good and not help but feel jipped because I might not appreciate the difference as much. Is that something to consider/am I making sense?
I don't have malicious intent but dude you're crazy. Why make tiny baby steps when you can make a giant leap forward and not waste money on headphones that you're ultimately not going to enjoy anyway. The headphone is always step number one as it provides the sound that you want, which is the entire reason you got into this in the first place. The AMP and then DAC are way down the line in terms of importance. Heck, making sure that your music is all in FLAC/320kbps will make a bigger difference in sound quality then a DAC/AMP. You're focusing far too much on secondary, no...tertiary items.
In short, headphones first.