This is convincing me that, at the very least, @philip is right that the CSV export should include the calendar dates. That might be a nice simple #UVI in fact. (No separate export though, just throw in an additional column.)
@chipmanaged, you are amazing. Thank you so much for the incredibly thoughtful feedback.
Until we get to this, I think the workaround, as you suggested, is to stay hyperaware of the deadline as end-of-day and remember to enter data after it as “yesterday”. Also I just remembered that @philip and I argued about this way back when in the context of the confusion of graphs being red despite not being due till tomorrow. I’ve gotten pretty used to it – red just means <24h – but it’s maybe not ideal.
PS: I’m laughing at the irony of “worse-is-better is better in theory”. I mean, in theory worse is, presumably, worse, but in practice it’s better. Something like that. That was probably your point.