One of the advantages of the Outside, when it comes to escaping the pursuing Humanoids, was its abundance of buildings. Because of that, Red never really had a hard time hiding from Humanoids or escaping by free running on top of the structures. Furthermore, the buildings provide shelter for everyone.
In the previous Runners Survivors that Red went through, he never had a problem with places with no buildings and he was confident that having a dull clearing on a map is sort of boring. If Head Cipher was trying to impress some sort of board of directors or investors, then he would put as many obstacles as he could to show the wide range of mobility that all the Humanoids have. Of course, that would make it easier to escape but at least the people watching the broadcast would be able to see everything.
