I don't know about Portlant being underrated where I'm coming from. All you hear about in urban design and transportation classes is Portland Portland Portland.
I would have to say that the highest concentration of underrated cities is in the South, followed by cities in the rust belt. The cities in the South are growing by leaps and bounds for a reason you guys, and they get knocked down so much simply because they are in the South, which is supposedly the backwards land of the Confederacy still. Rust belt cities are actually doing ok by rustbelt standards in this economy and some of them are pulling out of this bad economy and leading the way, so props. I also think smaller cities in large states with 2-3 large popular cities are overshadowed and underappreciated/underrated. My overall top 10 list:
1)
Pittsburgh (land of the Carnegies and the Mellons, awesome neighborhoods everywhere, great museums and universities, recently diversified economy and can't be considered "rust belt" anymore...think Biotech)
2)
Philadelphia (as Seth Myers said recently, Charleston = most friendly, Portland = most intelligent, and Philadelphis = also a city, LoL)
3)
Annapolis (Williamsburg can suck a D, Annapolis is awesome and stunningly beautiful, too bad it's nestled between DC and Baltimore and gets overshadowed)
4)
Richmond (heavily overshadowed by DC, but it has the Fan! and lots of companies HQ'd there, though my hometown did steal CSX
)
5)
Jacksonville (completely overshadowed by Miami and Orlando, but Jax is growing, has a great economy by FL standards, and is not nearly as boring as people who have never even been say it is...and most people who have been don't know where to go)
6)
St. Louis (friendliest town I have been to and one of the coolest, lots of STL pride!)
7)
Nashville (beautiful areas like Belle Meade, Vandy is there, and downtown is actually awesome...and not everybody listens to country, there is actually a diverse music scene there and Limelight is a lot of fun)
8)
Providence (though I hate everyone I know that goes to Brown and it shouldn't even be an Ivy, and I hate Prov. politics, the city is downright cool and easily overshadowed by Boston and NYC, and Newport is nearby!)
9)
Indianapolis (wow, it hits you with surprise like a frying pan to the face, this city has one of the coolest and most well done downtown areas in the country, and the Canal district, there is a lot to learn here)
10)
Cleveland (my favorite Ohio city, built around Standard Oil, this city used to be one of the greats and still has some of the best bones in the country, lots of beautiful buildings downtown and some nice areas around the lake, which doesn't catch on fire anymore!
)
I have to include 1 more:
11)
Kansas City MO (another MO city that just hits you with a frying pan like Indy does, lots to learn from KCMO and Country Club Plaza is literally one of the coolest areas in the country, also downtown has like 10 different restored and vibrant warehouse districts)