No need to feel apologetic or wierd to not feel there is a big enough quality jump for you. In fact imho it is actually normal!
From my journey into this hobby (and hifi also), the most obvious or bang-for-the-buck upgrade is always the headphone/IEMs. For the components, be it amp or dac or transport or power mgmt or other accessories the diminishing return is way steeper than the speakers/iem.
Honestly I would not be as impressed by Hugo/Mojo had I not spent/wasted a lot of time/money on various DAC. It is only AFTER I had experienced the more "hi-end" DAC I would understand how intricate the differences could be, and how expensive these incremental improvement can be. Over time (a long time) I start to be able to pick up the difference - first I learn what I like, then I stsrt to understand why I like a particular DAC. For me part of the amazement for Hugo/Mojo is actually in the context of how it compared to the (much) more expensive DAC. I am quite sure I will appreciate it less had I not went thru what I went thru with various gears. From an absolute perspective, you are absolutely correct that a $500 investment im headphone will yield more improvement.
I also find the source material also make a big difference ib my appreciation of a DAC. Here I'm not referring to the sampling rate or bit depth, but the recording and mastering of the music - crap in crap out. Hugo/Mojo do not make my crappy tracks sound better (like how my tube amp does by giving me a less accurate sound) or magically add more details, they just recreate whatever is recorded most accurately.
Hope this make sense. Cheers.
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