First off, thank you all for taking the time to answer this question.
After reading over what was said, I have to say that I like the intent behind the quest. I like the gist of the execution having it be done in recordings and how it surprises you with it. Very well done and thought out, but the dialogue... feel free to hate me... was awful for this quest,
It was so bad that I am still confused as to what they were really going for. First off, I thought it was a daughter and then yeah, he mentions being sick but I don't know.
It was like whoever wrote the dialogue didn't know what kind of feel to go for or what emotion for the speaker to have. And because of that, the last line didn't feel like a resolution.
Then Ryder's dialogue made it even more confusing. "I'm not sure I'm okay with this."
Why? What is it you're not sure about?
Now to be fair, it is possible that the people tasked to write dialogue for these quests are given a character limit and boy, can that mess you up when trying to write dialogue. Still, this could have been the most memorable mission in the game (for good reasons) and instead I feel the dialogue ruined it almost completely.