I'm surprised Asheville didn't make your list as it always seems to be in the top ten of everything I read about where to live. In the East, there is no prettier place than the Blue Ridge Parkway from Asheville north to the Boone/Banner Elk area. Of course, these are all just subjective opinions and varies from person to person but my problem with some of the towns you listed out West (where I lived for 16 years) are gangs, crime, and drugs. When I moved back East, first to North Carolina and then finally to a small Mayberry-type town near the KY/TN border I thought I had gone back in time 30 years. Living in Mayberry may not appeal to some but it sure is nice living somewhere where crime is *never* on your mind.
Marathon in the Florida Keys. Lived there for a long while and loved it. All the amenities you need and all the water, sky and sunshine you can handle.
I live in NYC but I still miss AZ a lot. Scottsdale may be one of my favorites. Then San Diego.. As you mentioned Shenandoah area is beautiful but extremely rural, it is good for B&B trips imo. The women observation in Minneapolis is right on the money, beautiful Scandinavian descent, friendly women and summers are to die for.. Chicago is all the best that NYC can offer in a nutshell, great food, night life and friendly people but the wind chill will get you in the winter. I guess Santa Fe may be very nice also, if you have good trading set up, love Southwestern food..
I live in Chicago and have been to a few of the places listed above. I also scan realtor.com alot to see where the deals are around the midwest. Granted, Chicago is a bit of a rip off and Cook County is in a financial nightmare with alot of cronyism and wasted bureaucratic spending. So, cross that off your list. Madison, Wisconsin is a nice place. I think its always a plus to look for areas to live with major universities. At the very least, you will have some culture and some youthfulness that will make the place more interesting. I might say take a look at Bloomington, Indiana as well. Have not been there in a long time, but again its home to Indiana University, presumably has a pretty good cultural scene and decent stores, etc and its dirt cheap. There are some really nice areas in the suburbs around Bloomington, including some huge developments on some larger lakes in the area. Prices seemed reasonable. Lots of 3500sf homes down there in the low 200's, with low property taxes. Insurance is cheap down there as well. It might be a place to look. There are also some nice areas up along the shoreline of Lake Michigan in the state of Michigan. Culture might be lacking, but the prices are very reasonable as well. Income taxes are a bit higher and I am not sure what insurance costs in the state, something to look into. In general, I can understand why many members on this board have wildly divergent opinions about the existence of a housing bubble or lack thereof. Areas of the midwest look like they have just kept up with the "true" rate of inflation, while obviously the East and West coasts have absolutely skyrocketed in appraised values. Still, there is no question in my mind that there are some good values if you scour that MLS on realtor.com.
We do not have the humuidity that Houston has and we have a great chain of lakes here that are awesome in the spring/summer/fall. Austin has a nice rolling hill country on the western side of town and the town is not too big like Houston or Dallas. Austin and all the surrounding communities is just over 1 million population with a ton of new young freshmen girls every year attending UT (The University of Texas....Longhorns). It does get hot in the summer but I don't think it is that bad since our humudity levels are lower then the Gulf Coast region. Property taxes seem to be lower here then Houston (I lived in Sugar Land for a year....until I escaped to Austin...LOL) and our housing prices are very good IMO compared to many of the over-inflated areas of the country. This town is the "live music capital of the world" and there is always something going on in town if you like to live it up all the time. If you have specific questions just PM me and I will give you more info.
that is one thing I don't really like Portland compared to city like yours. We don't have as many symphonies and rock concerts as larger cities do