Dude, you made me chuckle. Sometimes I want to hate myself more too.
Yeah, I totally understand where your pain points are, and there are probably a couple different answers I can give, one of them trickling into the post I want to do about product engineering over product management.
But I think a better answer might be this — instead of dates, or even with dates, use data. Build those features for which you have conclusive proof that they will add incremental value and revenue, the largest increments first. If you can’t prove a feature with data, don’t build it. Instead, spend that time building what it takes (maybe an MVP) to determine if that feature is worth building.