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I'm guessing maybe there's a bug in the consueling or drinking part that prevents this from happening.
In that 2nd play-through I mentioned above, I managed to broke Boris again the second time -- and together with Bruno. This time I didn't give any of them alcohol, but when both of them were back to normal, the achievement didn't pop.
So I started my 3rd play-through just for this. On one day I had Boris killed the civilian in Old Town, but that was not enough and he was still on depressed. So on the second day I had him broke into the Quiet House and took out the elderly again.
He was so broken when he came back to the shelter! Not even Zlata can talk sense out of him and he was just crying at the door way all day long in broken state, I can't even had him finish the meal and get the Well-Fed buff. And then the most ridiculous thing happened on the second morning. The achievement just popped out of nowhere! I double-checked Boris and he was still on depressed.
So long story short, if anyone is having trouble getting this achievement, your best bet is: