A mid-ranking Legion officer stationed in OE has been offered the hand of a well-to-do man (whom she has never met in person) back in Cyrodiil. She needs to commission a suitor portrait to send to this person. The officer is very much in love (with the letter and suitor portrait she has herself received, subject to much gossip and amusement among her fellow soldiers, as well as the rest of town) and wants the most exquisite portrait she can get. She knows of an artist brought up in Wayrest under the apprenticeship of the official Court painter who lives in Old Ebonheart. He traveled to Morrowind with Helseth and Barenziah, seeking exotic influences, and was sort of forgotten. The officer wants the player to convince said painter to do her portrait. Apparently, the Breton has been turning down potential patrons like the officer lately, becoming more and more reclusive within his workshop/gallery.
In order to help the client, the player will have to form a personal connection with the painter. Thus these first two tasks are more about proving their trustworthiness to the somewhat paranoid painter rather than actually fetching needed supplies.
1- The player contacts the painter, who makes no promise but asks the player to gather pigment-bearing plants for him, either by purchase or foraging the surroundings.
2- Returning with the plants, the painter requests a small number of clay bowls to mix the pigments into paint in.
3- On returning with the bowls, the player is tasked with fetching one more thing: the painter confesses that he relies on skooma for inspiration (implying this is the cause for his fall from grace with the higher circles of society), and simply cannot work without it. He agrees to do the portrait, if the player can procure some skooma for him.
As it turns out, the painter's normal Skooma dealer has gone missing and the player has to find him a new one by slumming it in Old Ebonheart's seedier part of town. Once this is taken care of, the painter will thank the player profusely and eagerly begin work on the portrait.