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The biggest elephant in the room in this list is Baltimore, Charlotte & Pittsburgh are full on major cities while Richmond, Charlottesville & Portland are not, so they are going to fundamentally feel completely different living in and around them than the former three.
(Apart from Richmond, VA) I'll stick to the big cities for now because I'm way more familiar with them.
Education - Tie. All have good schools in their metro. Their city propers, are meh-to-ok at best (for Pre K-12 at least) Crime - Charlotte is by far the safest, followed by Pittsburgh. Baltimore is unfortunately going through a serious crime issue right now but there are a safe areas in the city contrary to City-data stereotypes. Work - Depends on the job sector you get selected for. If your doing finance for ex. Charlotte is the place to be. If it's Health/Medical sector Baltimore is a power house with Johns Hopkins. Pittsburgh is an amazing blend of really everything so it's not a bad choice either. CoL - Tie. You can find nice units for $1600 in all 3 of the cities. That being said, Charlotte is growing at a ridiculous pace right now so it's going to become more expensive in the upcoming years. Baltimore & Pittsburgh are stagnant/declining in population so aren't seeing CoL spikes. Nightlife - Baltimore/Pittsburgh by a long shot if you and your wife want a night out whether it's bars/clubs/lounges etc. (if thats your thing). Charlotte falls short in this area compared to the former two Food - Baltimore if you like seafood, outside of that all 3 have great food options Entertainment - Tie. All three have multiple sports teams and have every "big city" amenity anyone would ever need Public Transportation/Airports - Baltimore has a metro/light rail, and has 3 major airports all within 30 min to 1 1/2 hour drive (4 if you include Philly's) Weather - Charlotte all day every day if you like warm weather. Baltimore/Pittsburgh do get a full 4 season though if you like that. Location - Baltimore sits in the Bos-Wash corridor and unlike the other two lies on a major body of water. Pittsburgh & Charlotte simply can't compete in that area as they are relatively isolated cities. Misc - Baltimore/Pittsburgh are substantially more urban from a built enviornment, Charlotte is not. Charlotte is going to have a lot more "breathing" room. If thats not your thing, it's going to be a turn off.
Baltimore has the best suburbs out of all the cities you mentioned. I haven't been in Baltimore more than a few, but I've visited relatives and friends plenty of times in it's suburbs in Owning Mills, Columbia, all the way To Landover. I consider it my "third home" if you will. I love the Area!
Pittsburgh, I've went to University about an hour outside of Pitt, the downtown area is my favorite although the transportation is a pain in the butt. Suburbs range from towns of less than 5k to Mid-sized full suburbs.
Baltimore is the best, most well-rounded city on the list.
Richmond would be my second choose. It’s the last city down 95 with any traces of the North East (won’t have any culture shock coming from CT). The suburbs are pretty sunbelt though. Great schools in the western and southern suburbs. Food, beer and art are exceptional but after a few years it will start to feel small (it’s growing quickly though, until this plague there was something new to do weekly).
Pittsburgh has a great downtown but the metro can be dreary (weather and economically).
Charlottesville is a lovey town if you are wealthy. It’s expensive with low(ish) wages. Very pretty, great food and music.
Technically Charlotte is a “big” city but you wouldn’t know it visiting. It has a pretty skyline but a small downtown area and not much else going for it. It’s definitely comfortable and may be a nice place to live, but there’s nothing interesting or remarkable about it.
Portland is the safest by far with probably no nightlife
Out of these I think you should pick Pittsburgh
I may disagree on Portland's nightlife a bit. While it's definitely not comparable to a big city, I'd be hard pressed to find a city of 60K people with better nightlife. It was voted Food and Wine's restaurant city of the year last year (or the year before, can't remember). It is absolutely one of the top food destinations in New England, and it's beer and cocktail scene is already well documented.
The bar scene would be down to personal preference. You probably won't find diverse nightlife, but if cozy pubs and breweries are your thing you'll absolutely love it, because it has those in spades.
Pittsburgh is a great city and obviously much larger than Portland. But if job market wasn't an issue, I'd probably pick Portland with it's coastal location and access to other New England cities. At least I'd pick it in the summer, ha.
Technically Charlotte is a “big” city but you wouldn’t know it visiting. It has a pretty skyline but a small downtown area and not much else going for it.
You obviously have a preference for older cities which is cool, but it doesn't seem as though your personal preference aligns with what the OP is looking for. This is evidenced by your statement that Charlotte doesn't have anything going for it besides a pretty skyline which is just patently untrue and you've got to know that. Also Baltimore is your first choice but has huge negatives in a few areas the OP is looking at which you didn't mention at all. I'd also disagree that Charlotte has a small downtown area but that's another discussion.
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