Summer in New York

It's the summer of 1990, and writer Richard Grayson -- about to turn 39 and having recently lost forty pounds -- has come up from Florida to spend the summer in his native New York City, shuttling between a friend's Upper West Side apartment where he's lived for the previous six summers and his grandmother's apartment on the beach in Rockaway, where she is suffering from depression and other problems of old age and is ultimately hospitalized for weeks.
For most of the 1980s, Grayson has gotten by as a writer through combining literary grants and income from part-time college teaching and computer education workshops -- and a scheme relying on constantly moving cash advances from the over 40 credit cards that Grayson accumulated during the Greed Decade. Now Grayson's credit card chassis is spinning out of control, with him $150,000 in debt. What do do next?
Grayson has previously published a dozen volumes of his diaries for the twenty years preceding 1990.