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It’s as he’s setting up the library so other hunters can come and use their resources that he realizes no matter what he does, it’ll always be about monsters. His hunting days may be over, but his life will forever revolve around the monsters in the closet.
He thinks about how he would have finished his law degree by now, settled down, had a couple kids. He takes himself out of the room with eons old books (making sure to grab the half full whiskey bottle,) to his bedroom, which he proceeds to detroy. He flips over his bed, tears a pillow in half, feathers flying (seriously, who still has feather pillows in the 2020s?) His night stand ends up in splinters, a smattering of half filled coffee cups end up shattered on the floor. He collapses against his overturned bed legs, the weight of everything crushing him. He falls asleep there among the rubble.
Dean and Cas come back from a trip to some bee festival Cas wanted to see the next day. Dean walks around the place, looking for Sam. “I know he likes to stay up late but this is nuts.” He mumbles, trying to find his brother. “All I wanna know is if he wants lunch.”
He knocks on his door briefly, barging in after no answer. He finds the destruction, the chaos, the discord in a usually tidy place. “Sammy?!” Sam shifts, disturbing his surroundings enough for Dean to find him. Dean traverses the room, crouching down next to Sam, giving him a once over. “You good?” Sam groans a little, fighting to stay asleep. Dean takes in the scratches littering Sam’s body. If the place wasn’t as warded as it is, Dean would have blamed something, anything else. But the bunker is more secure than Fort Knox (a place he’s broken into twice for cases.) He knows better. He calls Bobby knowing he’s not equipped enough to help Sammy through whatever caused him to do this.