Wrapping this thread up, yesterday I drilled the tank. I just couldn't get the return section to have a stable level of water in it with the hang on the back. My guess is my return pump just isn't consistent (jebao dcp), and fluctuations in its output was leading to changes.
With the single drain HOB it was impossible to set it up such that it was both quiet and self-regulating. My guess is that a 2-3 drain HOB would've worked fine, but at that point it was the same cost to buy a drilled overflow. I also didn't want to keep debating in my head if the problem was the HOB'ness or the pump or whatever. Drilling removed one more variable that I have to worry about.
I ran to Neptune, picked up an eshopps eclipse M, and drilled the tank. Drilling went very well, and was much easier on this glass than the previous rounds where I drilled 5-10 gallon tanks. Next time I'll probably just do that from the start, as was recommended here.