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Much of what these questions are asking about is the characterization of Ichabod Crane and his position in Sleepy Hollow society. Irving answers the first above-mentioned question with this passage: "The schoolmaster is generally a man of some importance in the female circle of a rural neighborhood; being considered a kind of idle, gentlemanlike personage, of vastly superior taste and accomplishments. . ." Back during the early 19th century, education was considered either a luxury, (because it wasn't necessarily a public right at that time, and only the rich could afford it) or a nuisance to the agricultural way of life. Hence, the schoolmaster was considered high in authority next to the parson; so, females were naturally drawn to his understanding of modern ways. He also taught voice lessons to many of the women in the area, but he was mostly desired because he played into the women's fascination with superstition and the supernatural. His hobbies also helped him to be accepted by the women. His book, written by Cotton Mathers, was a resource he could draw upon to entertain the womenfolk with new and interesting spooky stories. And since Irving describes the hollow as a place enchanted with superstition, Crane fit right in.
As far as descriptions are concerned, that Crane is lanky and not as good looking as Brom Bones; but this was not the greatest factor for a man's character back in the day as it is now. Crane's interests and ambitions are the characteristics which truly define him as Irving's hero. As stated in the story, "He was, in fact, an odd mixture of small shrewdness and simple credulity. His appetite for the marvellous, and his powers of digesting it, were equally extraordinary; and both had been increased by his residence in this spell-bound region."
This is from the excerpt "Ichabod Crane" from "The Legend of the Sleepy Hollow".
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