Well as much as I'd hate to admit it. It was the fuel filter. I replaced it with a new, slightly larger one and the problems have seemingly gone away completely. I'll post if it still fails but I doubt it will.
It must've been at the perfect restricted fuel flow where at a certain tank level the pressure wasn't enough to overcome the filter or something and it choked one of the cylinders dry. At 2 gallons left it would barely go above 6k and when I filled it up it fixed it, so I replaced the filter after that.
A month's worth of headaches and a $6 fix
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