Art Appreciation

Art Appreciation is a miscellaneous quest in Fallout 4.

Detailed walkthrough
Talk with John Hancock in Goodneighbor and ask him for work. He'll offer you a reconnaissance job to scope out Pickman Gallery. For the service, he'll give a base sum of caps but can be pushed to offer more with speech checks.

Go to Pickman Gallery, located Northwest of Old North Church. Raiders will be found around the outside and inside of the gallery, all looking for Pickman. Fight your way through them to the room immediately left of the entrance. Take the holotape titled "Message to Jack" off of a dead raider in the middle of the room, which is all Hancock will need. Exploring the rest of the gallery and killing the raiders is optional.

Return to Hancock and talk to him, initiating related dialogue where he learns what he wanted to and is pleased with your work. He'll then reward an amount of caps dependent of how many or if any speech checks were passed.

Bugs
This quest will become inaccessible if the player has already completed The Big Dig and gained Hancock as a companion, though it can be force started on PC using the command. However, Hancock will express dislike at having to go with the player upon their return, regardless of whether he did or not. This method also means the player cannot earn the potential 400 caps reward, since the speech checks are removed with the quest once Hancock has become a companion.