After Col. Potter finds out about his paid off mortgage, he thinks back to telling his wife there was housing for rent on the base. Base housing is not rented by service men or women. Base housing is a benefit for married enlisted men and officers. There are also bachelor officer quarters (BOQ).
Black Tuesday, the beginning to the Great Depression, happened in 1929, not in the 1930s. One would expect Winchester to be aware of this, regardless of the fact that his family wasn't affected by the Crash. In addition, there were no confirmed reports of stockbrokers jumping out windows, merely rumors and anecdotes.