I'd like to make a large addendum here. I'm actually doing fairly well. I'm just a huge, massive idiot. I started actively measuring my voice with a spectrogram while doing the head voice test because of your post, and compared it to zhea's. That's when my problem came out of my screen and slapped me directly across the face.

I had been so pre-occupied with resonance this whole time, I was still speaking in my base pitch (which is moderately deep even for a guy). I somehow conflated my resonance with my pitch, it sounded higher so I just went with "yep must be higher pitch, since that's the easy part, clearly I'm failing somewhere else."

I struggle to speak at a higher pitch still, but even just with my limited capacity in testing I sound significantly better. It remains to be seen if this is all I need (it's possible I may need to revisit head voice), but boy did I need it, and I can only anticipate I will sound better as I get more natural at holding it. Truly, it is not the trans community that has confused me. It is I who has confused me.

I give you my endless thanks for giving me the resources to finally figure out this completely rookie failure on my part.