I only brought rogues up because if I'm going to detail how it works, I'm going to detail ALL of how it works (which includes rogues).
Should this edge case be addressed? Yes. Delvin, Vita, and I all have bounced ideas around on how to fix it, but I think Delvin wants to finish his current update before adding another change in--which is good, because a focused Delvin means things get done sooner.
Someone should throw that guide I made on your wiki though, in the manual ideally, or it'll probably get lost again like the other times it's been detailed (or so I'm told).