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If you've seen her good ending with the dialogue you mentioned, you definitely should be getting the achievement.
From what you describe I can only guess there may be some sort of issue with the persistent save file with possible corruption or an issue with reading or writing to the file which prevents the process with the achievements from working as intended.
The only thing I'm not able to try is with a different steam account on my computers.
I couldn't understand why this would happen until I tried to get Adine's romantic ending on the non-DRM. But then, after doing all the steps, it wouldn't trigger. Then it clicked in my mind. It had been so long since I'd played last that I forgot her romantic ending might not be part of the core game. So I went to the workshop and sure enough, I was subscribed to Adine's Romantic Ending. One unsubscription later, another play through, and there was the good end notification.
Lesson learned, always check if there are mods installed if something's not working. How ironically fitting that the first ending I got for Adine this play through a few days ago was the mod's idiot ending.