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When did the drama happen? Is Willy considered as a typical middle-class American at the time?  I know the play is first performed in 1949 but I am unsure if the characters lives in the 1950s or not.

The setting for the play is 1949, so it is contemporaneous with its appearance on Broadway. Post-World War II was a time of unprecedented prosperity in America, and sales jobs were widely considered the way for otherwise unqualified, mostly uneducated, young men to get ahead. Because the country was undergoing important changes, such as greater access to all parts of the United States (via brand new highways that extended into previously undeveloped areas--for example, Las Vegas) at the same time it was creating new products that were mass-produced and inexpensive to produce, the time for salesmen had come. Willy Loman was riding that wave. Willy was lower-to-middleclass. He was providing for his family, he had a house, but his income was dwindling because his sales techniques were no longer working, and so his status is threatened by his poor performance at work.