I've lived in the Ann Arbor area most of my life and $1,400 for an Ypsi apartment seems pretty steep. I'm guessing that's in Depot Town? Ypsi should not be your first choice, especially if you've lived in San Diego and NYC.
As far as COL, Ann Arbor shouldn't be anything out of the ordinary from the places you've already lived. It's just steep compared to the surrounding Michigan counties.
Ann Arbor is an awesome place to live and I have no doubt you'll enjoy Michigan. Except the weather... it's a wet, sloppy mess currently.
