Name this US city and related urban trivia!

Thanks and you're persistent. I had to crop out the large "Settles Hotel" sign on the top of the tower to make it a challenge!
 
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This is the only city still unsolved which surprises me because the clues lead to relatively stress free research and it's not some podunk town.
 
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This northern city of 12,500 probably has the tallest building (18 floors) for the smallest population in the country not counting a few rural casino hotels. The residents of this area believe they live in the best part of the state and look down upon the rest of it!
 
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The courthouse, riverfront arena and the 15 story West Virginia Building are definitely the landmarks that I've always focused on. Sad that such an important regional hub has lost population for seven consecutive decades and is down to 46K from a high of 86K. Charleston, the largest city in WV has only 2,000 more residents than Huntington and has lost population for six consecutive decades!
 
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You are becoming legendary and did not miss the subtle U.P. clue. (y)
 
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Became the largest city in the state from 1980 through 1990 which really annoyed its slightly more urban competitor to the south! It appears that second biggest will have to due for this regional center of commerce and gateway to the vast outdoors. And if you believe in them, this one would be considered friendly.
 
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Portlander said:
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Became the largest city in the state from 1980 through 1990 which really annoyed its slightly more urban competitor to the south! It appears that second biggest will have to due for this regional center of commerce and gateway to the vast outdoors. And if you believe in them, this one would be considered friendly.
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Casper, Wyoming
 
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So this is a shout out to the city I spent portions of my youth including high school due to my father serving a career in the military. It currently has a population of 72,000 which is more than my hometown of Portland! However, it has the smallest downtown for a city of its size on the east coast primarily because it had less than a 1000 residents in 1940. In it's hey day, the main drag was a carnival atmosphere at night and packed with the typical establishments that cater to the military such as bars, the USO, liquor stores, pawn shops, bail bond offices, telephone exchanges, easy loans, tattoo parlors and after hour lounges. Women were not encouraged to visit the often rowdy downtown area and in the late 70's a major effort to clean up the city and revoke liquor licenses was effective. Now the area is pretty much desolate with the exception of the courthouse, bail bondsmen, attorney offices and a few other city and county entities. If I shared the branch of military it would be too easy! *** Now that DesertMainiac has come up with the answer, the main street in the photo is Court Street ***
 
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Portlander said:
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So this is a shout out to the city I spent portions of my youth including high school due to my father serving a career in the military. It currently has a population of 72,000 which is more than my hometown of Portland! However, it has the smallest downtown for a city of its size on the east coast primarily because it had less than a 1000 residents in 1940. In it's hey day, the main drag was a carnival atmosphere at night and packed with the typical establishments that cater to the military such as bars, the USO, liquor stores, pawn shops, bail bond offices, telephone exchanges, easy loans, tattoo parlors and after hour lounges. Women were not encouraged to visit the often rowdy downtown area and in the late 70's a major effort to clean up the city and revoke liquor licenses was effective. Now the area is just desolate with the exception of the courthouse, bail bondsmen, attorney offices and a few other city and county entities. If I shared the branch of military it would be too easy!
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Camp Lejeune
Jacksonville, NC!
 
These other city proper populations are somewhat irrelevant in comparisons to Portland, ME. The metro area is the true measure of a city's size, and another city core just a little over 90 minutes away from Portland has a metro pop of 5 million (Boston). Over the last several years I've had to go to some of these smaller cities in the mid and southwest, and socially and culturally and economically, it's comparing apples to oranges with Portland, ME. As the Hardshore Distilling owner transplant from Brooklyn said to me, "Portland is a suburb of Boston." People who commute into Manhattan often spend 1-2 hours with their commutes, and so do many others around the U.S. I think in the not-too-distant future Portlanders will wake up one day and realize that Portland is no longer "Maine." (Residents from Boston drive up or train up regularly for Seadogs games and concerts and the foodie and bar scenes.)
 
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And today there are 4 yachts in the Fore Points marina as the occupants walk up to Twelve for a bite or drink. The GM and the Sous Chef co-owners are from New York. Not Maine in Maine, as I like to say.
 
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This city has a population of around 70K, worthy enough to be classified as a metropolitan area and has a regional airport that is served by a major airline. The downside, it is quite possibly the most isolated urban area for it's size east of the Mississippi and residents have to travel over 35 miles to reach an interstate highway. To add to the middle of nowhere blues, the nearest larger sized cities (180K plus) are all located over 100 miles away in almost every direction! Enjoy.
 
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Portlander said:
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This city has a population of around 70K, worthy enough to be classified as a metropolitan area and has a regional airport that is served by a major airline. The downside, it is quite possibly the most isolated urban area for it's size east of the Mississippi and residents have to travel over 35 miles to reach an interstate highway. To add to the middle of nowhere blues, the nearest larger sized cities (180K plus) are all located over 100 miles away in almost every direction! Enjoy.
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Going to the Deep South!
Dothan, Alabama
 
I may have to ban you from the game, that was not an easy one!
 
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