Don painting over a water-stained wall in Anna’s house is a device used in “The Good News” to advance the storyline of his visit to California and (apparently) close that chapter of his life. Ostensibly, the discoloration is the result of a leaky roof. Anna tells Don that she has fixed the roof but not gotten around to removing the stain.
The morning after finding out that Anna is dying, Don starts to paint over the stain. Anna correctly points out that covering just that small corner, rather than the entire room, with fresh paint isn’t really going to solve the problem (the newer paint won't completely match). However, the act serves both as a metaphor for Don’s feelings of helplessness in dealing with Anna’s illness as well his coming to terms (albeit perhaps temporarily) with his former identity
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