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the first cities that come to my mind are Atlanta Charlotte and Austin. If you're into Rap/R&B Country and/or rock music Atlanta/Athens, GA would definitely be my 1st choice
I think there's other factors (location, weather, size/population, cost, types of people there, safety, etc) you need to weigh which might impact your choice. If I were in your shoes (I'm close if you change the career and the relationship status), my choices would come down to Chicago (where I currently live), NYC, Seattle, DC, and San Francisco. Those are my choices because I like really dense, older cities with great architecture and great culture (the same criteria you used).
There are other cities which fit my criteria like Philly, Boston, Baltimore, New Orleans, etc that also fit my criteria but I didn't fall in love with them when I visited them. If I were you, I'd make a list of the top 3 places that fit your criteria and really interest you and I'd use some of that savings money to travel to those cities and whichever you like best, move there!
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