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All three have areas that work by your criteria. I guess the question is what other criteria/preferences do you have, what job prospects/offers you have (as well as what neighborhood that job is in), and which of these do you have any existing friends or family (that you like) in.
But past their prime with large portions of their populations that want to live in the past instead of adapt to the changes around them.
In other words, you have no idea about the three cities listed, and are of no use to the original poster, but you just want to hear yourself talk anyway.
Ann Arbor has everything you'd want in a liberal college town, including an arts scene relative to its size, but it's far different from the other two to compare. Cleveland and Pittsburgh are fairly comparable, but Cleveland's arts scene is more traditional (symphony, theater, museum) while Pittsburgh's is a bit more organic. Cleveland has more crime and better health care resources, but overall I'd say to visit both Cle and Pitt to see which you like better personally.
AA is a great town but should only be chosen if you're specifically looking to leave the rat race for a more "village" type atmosphere.
I agree with all of this. My only addition would be that if public transit is important, then Pittsburgh wins outright.
Cleveland has a bit of a "Charlie Brown" ethos, where they feel picked on and are therefore striving to show how good they really can be.
Outside of that, Cleveland and Pittsburgh compare pretty evenly.
Thanks for the feedback thus far. Most if it was helpful.
I know that Ann Arbor proper is smaller than both cities of Cleveland and Pittsburgh, but it seems to have a lot going on, and that appeals to me. As I mentioned in my initial post, I am open to either a large city or smallish town.
My reasons for moving...
I want to get away from the noise and congestion and high cost of living in NYC, as it has lately become unbearable even though I pay rent far below market rate. I have lately had to admit that all my years of living here have worn me down, and I am very unhappy. Of course, I know that wherever I go, there I am -- I have to create my own happiness from the inside, but one's circumstances and surroundings play a major role. I am often depressed that after so many years here, I am still struggling to get by, and yet I know my last salary would be quite comfortable to live on in many other places. However, I am still a night owl, so I don't want to live in such a small town that they roll the sidewalks up at 9pm!
Lately I have had to admit that I never "made it here" as the song says. NYC has kicked my arse and this upsets me. Despite my apartment being below market rate, salaries have not kept pace with expenses here, and when you are in your early 50s, you are not as likely to get hired for the better jobs and don't want roommates anymore. If the money I could make here was actually commensurate with the COL such that I could enjoy all the wonderful things we have here, I'd stay. If I made enough money to afford a better apartment with thicker walls on a quieter block, I'd stay. My rent being low for NYC standards has effectively trapped me where I am, unable to afford something even just a block away where it is quieter. I think I am really ready for a change.
The noise levels here have gotten to me the most. When I look at how hard it is to afford an apartment that is well below market rate, just to live in a place where I am assaulted every day by horns and sirens and loud neighbors and dogs barking (a dog daycare center moved into the building next to mine and the barking is nonstop from 7am to 8pm - complaints have done nothing to fix that). Where I live is a great neighborhood in so many ways, but my street is just so damn noisy. I hate that I can't afford to move anywhere within NYC, sadly - unless I leave Manhattan, and I really don't want to live in an outer borough.
As far as work, I have experience as an executive assistant but that was a long time ago and isn't my preference. I've always just hopped around to do what appealed to me, and my resume looks like a hodgepodge of stuff. Most recently I worked as a manager of an independently owned retail store, but I am in the process now of starting my own online business, which hopefully would do well enough to support my living in a number of places. So, I won't be ready financially to move until that is established and bringing in an income I can count on. If necessary, I will supplement that with either part-time work or some independent contractor work I used to do and could easily pick up again pretty much anywhere. Right now, I want to look at possibilities so that I can make plans to visit and then come up with concrete goals for getting the heck out of here.
And yes, I would consider almost every part of the US, except the deep south because I don't like extreme heat and humidity. I prefer four seasons and enjoy cooler weather, don't mind the winter and snow at all. It would seem weird to me not to live near the ocean, but I am open. I thought I would compare different cities across all regions to narrow things down and the cities in the title of this thread are just a starting point. And I should add that, no matter where I go, I will have to prepare by taking numerous driving lessons to become a confident driver. I've lived in NYC for over 25 years, and can count on my fingers how many times I've driven a car. I've never owned one either, so that would be another learning curve, but I am willing. I guess that's why public transportation and a walkable downtown is important to me. If I do buy a car, I wouldn't want to live somewhere that requires driving for every possible thing I would need. I would rather take a walk or hop on a bus/subway for a lot of needs, and leave driving for longer or special trips.
Places I've visited that appealed to me, for various reasons are: Camden/Rockland, ME; Asheville, NC; the Berkshires, MA; Nantucket/Martha's Vineyard/the Cape, MA; Chicago, IL; Knoxville, TN; Philadelphia, PA. Some of these places I haven't been to in a long time, and may not be so affordable, but it is more the feeling of the places I am trying to convey. For example, I love-love-love the feel of Camden and Rockland in Maine for vacationing but I think it might be too quiet and sleepy in either town for me to think about year-round living.
As far as further west, besides California which does not appeal to me at all (because earthquakes), the only places I've visited were Boulder, CO back in the 90s, St. Louis, MO, and Santa Fe/Abiquiu, NM more recently. While I enjoyed those cities, I didn't really see enough in any of them to know what they're like. I don't recall thinking I'd want to live in any of them, although I'd be open to learning more about all of them. I am a creative, artistic woman, divorced, and want to be somewhere conducive to dating and socializing (though that doesn't have to mean only people in their 50s at all! I make friends of all ages!).
I think you'd like Ann Arbor, TBH. Large college towns are great even for people in their 50s and 60s because they appeal to intellectuals and others who simply want to be in a positive-learning environment. Madison WI works for this also. Cleveland has a great collection of neighborhoods, both in and out of city limits, but unfortunately there are swaths of forgotten ghetto areas which divide the great parts of downtown and the west side from the prosperous university/arts district and desirable eastern suburbs. I think you could be happy in either place and both would give you a higher quality-of-life and more bang-for-your-buck compared to Manhattan.
Thanks, from what little I've read about Ann Arbor, it does seem right up my alley - but I'd like to gather info on a few places. Interesting what you mentioned about Cleveland - in the store I managed, we had a few customers who would visit from Cleveland regularly and buy expensive stuff. So that, along with the Rock&Roll hall of fame/music scene, are what got me curious about it.
For the person who asked about where my friends or family live, that isn't a factor at all. I don't have that large of a circle of friends and haven't socialized much at all because I've been so focused on surviving - so I am happy to go somewhere new and make new friends. As for family, most of mine are in NY, NJ, and CA, and I hardly ever have contact with any of them, so it's a moot point.
Oh, I forgot to mention another reason I want to move away from NYC - I am really tired of living in a city that is often a target for terror attacks. Yellow alerts and orange alerts and helicopters overhead are scary and I'm over that!
Yeah I moved from the Bay Area eight years ago..got burnt out on the long commutes and being harrassed every ten feet by someone wanting something from me. Midwestern people at least respect your personal space for the most part. Cleveland has a lot of residential downtown; the west side has a couple gentrified neighborhoods (Ohio City & Tremont) with coffeeshops and brewpubs, and the east side (past the ghetto areas) has the museum district, Little Italy and area with the main Cleveland Clinic campus. The eastern suburbs are also really nice, diverse, with a lot of dining and nightlife options. I'm not familiar but from what I've read they really have a thriving theater scene relative to the city's size also.
If you like the Berkshires and like the feel of Manhattan, perhaps you could also look into the cities in the Albany-Schenectady-Troy area. It is very close to the Berkshires and other smaller mountain ranges, there are neighborhoods with row houses, last call in that metro is actually 4 AM, it is actually a steadily growing area, all 3 of the center cities in the metro are diverse, there are walkable neighborhoods and it is close enough to NYC that you can visit as often as you could. It is also close to artsy towns/cities in the Hudson Valley like Hudson, Catskills, Kingston, Saugerties and New Paltz, among others. I've also heard positive thing about CDTA, which is the area public transportation company.
Since you are starting your own business, you can't beat Cleveland for the low cost of living!
Wouldn't Pittsburgh be similar in that regard?
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was helpful. 
