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It's simply designed to punish the player progressing, rather forcing running around the entire map talking to every npc to see if there was some sort of hidden activation within a single quest to progress others. The first game did this too, its kinda awful design but I get they're trying to push you into a new game plus so you can experience and fix choices. Your first play through is always going to be a ♥♥♥♥♥♥ throwaway play through, this is just how DD is.
Maybe give her a few more gifts to compensate and see if that works.
I also experienced not being able to quest romance with wilhelmina so I finished the game twice so I could romance wilhelmina lol
In short do it in NG+ and just remember to keep Coronation prolonged and wait a day to progress side quests / activate them.
also: "i don't like the consequences of my choices because they weren't explained to me beforehand!"