This task is made somewhat easier if the Canvas the Castle quest is active, as it gives you a key to the private quarters, allowing you to sneak around unchallenged. One option is to steal the glasses and pitcher from the bedroom of Countess Arriana Valga in Castle Chorrol which contains five silver glasses and two silver pitchers.If you've killed him for a Dark Brotherhood quest (or just on principle) you can find his house key on his corpse. The pitcher and all four glasses can be found in Alval Uvani's house in Leyawiin.In the "Chapel Hall" area of each city's chapel (except for Kvatch).An additional silver glass can be found on a table nearby. The Chorrol Mages Guild has more than needed to meet these quest requirements, and you can grab them without stealing once you've joined the Mages Guild: one of each lies on the table next to the entrance door, two of each on one shelf and three more glasses on another shelf in the second floor library.You can steal the silver pitcher from almost any home, although the silver glasses can be harder to find. He gives you 50 gold to cover the expenses, but there is no requirement that you must buy the items. He is her "secret admirer" of sorts, and wants you to find a silver pitcher and four silver glasses.
To receive training, Pranal first asks that you buy Malene (the Roxey Inn's publican) a gift.
Valus Odiil, although not a trainer, will also provide the reference. The only advanced trainer who can give you the master training reference necessary to start this quest is Varnado in the Imperial City.