In my experience, I have noticed a direct relationship between how complicated a problem is and the results that come from working with the more complicated issues.  This is particularly true when the complication is not man-made.
In my previous years as an employee to landscape architecture and planning consulting offices, I would seek out the projects that required greatest challenges.  I understood that these projects would be very difficult, which is what really got me excited to work on them.  More often than not, the complications were related to intense topography complications (too steep or too flat in rare instances).  In more recent years, it seemed that I would go after the projects that may have had a great amount of objection from adjacent land owners.  These project got me excited because I knew that there was a place in between where both parties could meet and the results from the project would be that much greater as a consequence.  This held true, in my opinion, during the entitlement process for the Gleneagle Patio Homes at Gleneagle Golf Course along with the clustered, compact development planned at The Mountain Preserve near NORAD in Colorado Springs.

Deadwood, South Dakota, Aerial from Google Maps.

For the vitality of cities and the ‘true creation of place’, I feel that this definitely is true.  Have you ever noticed that the greatest places and cities are typically a result of great complications, namely a confinement of land around them?  Generally, this is caused by something natural such as a valley, steep conditions, rivers, or other bodies of water.

Off of the top of my head, the following is a brief list of cities that have benefited from the natural growth boundary: Deadwood, South Dakota; Vail, Colorado; Manitou Springs, Colorado; Manhattan, New York; Boston, Massachusetts; Honolulu, Hawaii; Eureka Springs, Arkansas; South Padre Island, Texas; Nantucket, Massachusetts; various other Ski Resort Towns; and South Beach, Florida.

There are a few instances where the condition is artificial and imposed by man in the form of urban growth boundaries.  Cities such as Portland, Oregon and Boulder, Colorado are examples of the urban growth boundary.  In Portland, the success of the urban growth boundary has been quite effective in the redevelopment of the city.  Boulder’s growth boundary has yet to see significant results of its urban growth boundary in terms of redevelopment, however it has seen increasing property values.