Final answer:
F. Scott Fitzgerald, known for his critique of the Jazz Age in works like The Great Gatsby, is the author who experienced genteel poverty and crafted novels that questioned rather than offered clear answers.
Step-by-step explanation:
The author who was born into a prosperous family but experienced genteel poverty due to his father's bankruptcy and death is F. Scott Fitzgerald. Fitzgerald was born in 1896 into a middle-class family and became known for capturing the spirit of the 1920s in his works. His novels, such as The Great Gatsby and This Side of Paradise, offer a critical view of society and are considered sophisticated social satires. Unlike the characters often found in Charles Dickens's or Jane Austen's work, Fitzgerald's characters did not present clear moral lessons but rather embodied the complexities and ambiguities of American society during the Jazz Age. Fitzgerald's writing not only serves as a critique of the wealthy and the quest for the American Dream but also reflects his own personal struggles with financial instability despite his success as a writer.