Thanks everyone for the replies. Cleveland seems to get a bad rap, but hearing all these replies i'm optimistic.
In Portland, the ideal place for me is the "Pearl District", I also like "South Waterfront"
I'm open to staying in a more suburban place too, but really like the idea of living somewhere newer. So far I'm leaning toward checking out Warehouse district and Tremont. I have a friend in Beachwood who is pushing for that, but i'm not sure there is anything newer out there, I visited the Hamptons and it seemed a little older.