Portcity, a few cities for you to check out that have less than 100K with dense downtowns and impressive skylines for their size: Greenville, SC, Charleston, WV, Asheville, NC, Harrisburg, PA, Binghamton, NY, Huntington, WV and Jackson, MI. The smallest city with the tallest skyline (thanks to Phillips Petroleum) might just be Bartlesville, OK with only 38K. Battle Creek, MI (cereal) is another small city that has bragging rights to two 20 story art deco towers! Like Portland, many of these municipalities have very small city limits which keep the population counts considerably less than their counterparts but their metropolitan populations (MSA) can be substantial in comparison. Enjoy exploring!