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Land-use
A quick Pittsburgh - Portland comparison 
The irony is that Pittsburgh and Portland are probably more similar to each other geographically and structurally than any other city in the U.S.  But all similarity stops with their public policies.
Similarities
  • Both have compact downtowns which were built to a pedestrian scale with small city blocks and narrow streets.
  • Both have beautiful rivers through the middle of the city with an number of bridges that area residents use daily as just another street crossing.
  • The hearts of both cities are geographically constrained by their rivers and mountains (though someone from the Rockies might discribe the mountains in either city as large hills).
  • Both have more cloudy days than sunny ones.
  • Both have a large usage and dependence upon public transportation.
  • Both have a large number of historic buildings built around the same times.
  • Both have significant cultural assets of museums, theater, opera, symphony, etc.
  • Both have had severe air pollution problems in the past which they have cleaned up, yet they must still struggle to keep the air clean and meet new standards.
  • Both have a history as working towns with considerable industry and changes in manufacturing and business practices have profoundly affected their local economies.
  • Both have a lot of Pittsburghers living there.
Differences
Officials in Pittsburgh have sought to turn the city into a center suburb; the latest effort is to convert the downtown into a central suburban service area, primarily for the benefit surrounding counties. In the  1970's, Portland decided it wanted to be a "city" and not just any city but a great city.  Portland has made a conscious effort to protect its urban character and enhance the city as an urban space.  While the city provides services for the surrounding areas, it does so on its own urban terms and exists in form and function primarily as a space for the use of those in the city. 
Nine times out of ten when the city planning department uses the word "urban," the word that actually applies is "suburban." Portland's planning department is conscious of the urban form and actively promotes real urban design.
The vision of all things for the region is "bigger, larger, and more suburban." There is a conscious effort to keep the design of buildings human scaled.  After a defititely automotive-scaled, suburban-styled skyscraper was built in downtown Portland, there was a public outcry and special zoning and planing restrictions were enacted to protect the urban form and prevent its replacement with suburban styling.
The official goal is a de-densification of the city and the region as a whole, both for residential and commercial uses. Portland's planning department is actively encouraging density enhancement and has created architectural plans for the conversion of a number of single story buildings into multistory buildings to add capacity and increase urban densities.
All things old should be leveled to make way for the new temporary structures of modern construction. Portland holds a respect for its history ande the existing.  The conversion examples created for density enhancement do not demolish any of the existing buildings, but, instead, are done as supplemental to the existing, even retaining the original design character when it is nothing outstanding.
The official public policy is to subsidize expansion of the outer suburbs, amidst a continuing de-population of the metropolitan region.  Portland residents have overwhelmingly insisted that the expansion of the suburbs be contained, and it is engrained public policy to do just that.
Pittsburgh has had a super-concentration of wealth among an ultra-wealthy aristocracy.  This aristocracy has patronized the general public with donations for civic endeavors while dictating the public policy for much of the city's history.  As the end of WWII neared, the ultra-wealthy families and the corporate heads formally organized their efforts and created the "Allegheny Confernce on Economic Development."  This body has effectively functioned as a corporate state, determining public policy and making sure it is implemented.

As arms of the Allegheny Conference's policy efforts, the Regional Industrial Development Corporation (RIDC) was created to administer their policies among the private sector and the Southwestern Pennsylvania Regional Planning Commission was established to administer their policies through the public sector. 

To provide an effecient means of coercion for expediting their policy goals, a new instrument was conceived with the power of eminent domaine.  Given the title of Urban Redevelopment Authority (ULA), it has repeatedly forced private owners to surrender their properties in order that they may be conveyed to new (usually more wealthy) owners who will use their expropriated properties within the goals set by the Allegheny Conference. Copied around the world, the URA model has probably been the single most distructive implement in the suburbanization of the world's cities.

 Portland has its share of wealth, just as any city, but it has had no superconcentration as in Pittsburgh.  As a result, the people have had to be more involved and watch out for themselves, and the average person tends to more readily take an active role in community affairs. 
Pittsburgh Mayor Peter Flaherty sought to put an end to the destructive "urban renewal" process initiated by the Allegheny Conference and he even ordered that the URA be abolished, but before he could succeed in instilling a new political legacy, he left to become U.S. Assistant Attorny General in the Carter administration. His replacement as mayor immediately restarted the conversion of the city into automobile-scaled, suburban-styled, mega-projects, and the present mayor wishes to complete the transformation so that there is nothing left to save. Portland Mayor Goldsmith similarly sought to refocus the urban policy in his city to one of preservation and enhancement of the urban form. However, he stayed on the job until he moved to the state capital as govenor, a position which enabled him to ensure continuation of his policies. 
Pittsburgh has had a long history of professional sports, from the first professional hockey team to the major league sports teams of recent history; team championships among all the sports have been as or more commonplace in Pittsburgh than in cities several times its size.  Portland has a major league basketball team, a minor league baseball team, and no professional team. 
Pittsburgh has been experiencing a declining population since the 1950 census which followed the enception of the URA and its policies of "urban renewal" (or conversion of the city into inferior suburban projects).  Between 1970 and 1990, the entire metropolitan region experienced an 11% decline in population while spreading out that which remained over 30% more area.  The most reasonable demographic projections indicate that we can expect a continuing decline for at least the next 15 years. Portland has been experiencing a continuing increase in population which had it add 100,000 new residents in a 4 year period earlier this decade, and they expect to have 400,000 more in the next 15-20 years.  With the increase in population, Portland has taken dramatic steps to contain the expansion of utilized area, and most residents find that to be one of the great attractions of that city. 
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