Thanks for reading. Hope is helpful!
About that last point, I see how that's a design decision that could be taken. Leaving more room for "mistakes", and not every raven been worth to improve as you mention. I guess the main problem I see is the combination with point 4. Given your lack of info by default on what contracts lay ahead, those mistakes are more a cause of that than actual mistakes. Having unlocked all patrons once gives a very big advantage in a following playthrough. And while is normal that experience in a game helps you, it feels a bit "unfair" that is something you can't really tackle in that first playthrough at all.
That been said, it ocurred to me that maybe a way the granularity could stay and be maningful is if you include some variability in the deliveries (weather conditions affecting the birds, or maybe the contracts themselves would not neccesarilly exactly always have the same distance and time range for delievry as happens with paymens now). It would mean that every little extra in any category could be useful and one would have to decide what to prioritize.