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The OP asked "which city is the most overpriced for what it has to offer?" I think we are getting away from the question. Sure some cities may be overpriced but they offer more than other cities for that price. I just moved away from Portland for that very reason. I just wasn't getting enough bang for my buck. The prospect of huge rent increases of anywhere from $100.00-$300.00 a month each year wasn't worth it not to mention the high cost of everything else.
I have to tell you, the rent (and also home buying) situation here in Portland is spiraling upwards, out of control.
If you want to live anywhere decent in the city limits, you are looking at $1000 for a small studio.
Belmont/Hawthorne is getting crazy expensive!
If you thought it was getting bad when you left, I have to say that you left Portland at exactly the right time.
I'm glad you are happy in Cleveland!
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