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I guess that "failure" here is some kind of foreshadowing: I failed to rescue Joel, made some wrong decisions.
Overall, it took me too long to get strong enough to survive in the catacombs. Neither found my father nor the pirate treasure. Though I got the bad ending I love this game and will do better next time.
You have to look for the "special gift" that the chief thief (or your patron) left you somewhere near his office, as terk mentions right before you go there.
It will help with the door
Who gives you the quest on the final night then? I was taken by terk and told to break into the rogue teacher office to get the black bird, and that my patron left me a present by the rogue teachers office. Then I looked through the halls and found and envelope in a painting that gave me a magic key that opens the door after you disarm the trap
Then after dinner on the last night terk takes me and tells me my patron is pissed off at me and I gotta go get the raven or be expelled, and then said the patron left a gift for me in the hallway and this was my last chance to help him.
I found a magic key hidden behind a statue of a bard, just outside the classroom door
So the message in that case seems to be – if you get rid of Terk, you will destroy your future, unless you are 'Rogue of the Year'. That's not just a bad ending, it's a miserable one.
Fun fact: It seems, I'm in some kind of 'endless mode' now:
https://steamcommunity.com/sharedfiles/filedetails/?id=1446555813
If I don't go to bed, I'll be able to play forever (on a one apple per day diet).