In "The Ransom of Red Chief," why did Sam and Bill decide on a semi-rural area rather than the city?

In those horse-and-buggy days a very large percentage of Americans were subsistence farmers. There were many small towns dotting the Midwest because of the transportation factor. It would be an all-day affair for a farmer to drive into town in a wagon pulled by a horse or mule and then get back home again. There probably was no big city within hundreds of miles of the town of Summit. Sam and Bill themselves were small-time crooks who preyed on simple country folk. They wouldn't have known how to operate in a real city. They wouldn't have known how to communicate with city people. They might not even have known how to find any children in a city. They were relatively sharp compared to country people, but they would have been like country bumpkins in a big city.

Consider Sam's plan to collect the ransom. He was going to be hiding in a tree right up above the drop-off site. That was the extent of his thinking. Imagine trying to stage a kidnapping in a city with that game plan! Cities have lots of crime and are prepared to cope with it by having efficient police forces. Those small towns of O. Henry's day had little crime and therefore little police protection. It was nearly impossible, for instance, to rob a bank and make a getaway with a horse and buggy. Men would grab the horse by its harness, and others would stop the buggy by throwing their canes between the spokes of a wheel.

Crime escalated in America when cheap, mass-produced automobiles became common. It was cars that created gangsters like John Dillinger, Pretty Boy Floyd, Bonnie and Clyde, and others. They could rob a bank and be twenty miles away by the time the law ever got there. The excellent 1967 movie Bonnie and Clyde, starring Warren Beatty and Faye Dunaway, is good entertainment and also good American history. The film shows how automobiles were changing America. Nowadays towns like Summit are dying because automobiles make it possible to drive much longer distances then was possible with horses. Country people are doing their shopping at huge Walmarts and other big-box stores, while the little shops on all the Main Streets are standing empty and boarded up.

O. Henry's "The Ransom of Red Chief" is good entertainment and good history too. It shows what small-town American life was like in the 19th and early 20th centuries.