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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.
Not a fair comparison for Ann Arbor in my opinion as it's much smaller than either Cleveland or Pittsburgh. Ann Arbor nails all of your criteria and gets you out of gritty/dirty urban living if you're looking for that while the other two arguably could make it worse depending on location.
They are places all located in declining rust belt states.
Ann Arbor is certainly not declining, and it is not in a declining state.
To the OP- go to wherever you have the best opportunities. I went to U of M in Ann Arbor and CWRU in Cleveland. While people are saying its not fair to compare Ann Arbor with Cleveland and Pittsburgh, keep in mind that Ann Arbor is part of the Detroit metropolitan area of 5.3 million people which is larger than both Pittsburgh and Cleveland. So, no, you are not moving to a small town. And if you want to compare city by city, you might be surprised at how expansive and pedestrian friendly Ann Arbor is. A lot of interesting people from all of the country and world and lots to do.
I would also say Pittsburgh is great. In fact, it is one of my favorite cities in the country. There is a lot to do, cost of living is low, great restaurants, and the views of the hills are beautiful. Pittsburgh is a big city and also a college town at the same time. It is a wonderful place.
Cleveland is fine. In my personal opinion, it doesn't have that buzz you find in Ann Arbor or Pittsburgh. Cleveland has a downtown, University Circle, Tremont, Detroit-Shoreway, Little Italy, Coventry, and Shaker Square. Most of those places are small with just a handful of restaurants (except downtown). However, it doesn't have the pedestrian feel you get in Ann Arbor or Pittsburgh with crowds of people walking down the streets and going in and out of establishments.
But all 3 are good. Pick the best opportunity for you.
I agree that Ann Arbor fits just about everything in the criteria and even though you didn't mention it, it is close to Detroit International Airport as well if or when you want to fly.
Also, are you open to other areas? I only ask because you may not have to even leave the state or region to find what you are looking for.
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.
And most of THOSE people live outside of the three left-leaning cities the OP is asking about.
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