North Shore Place I and II would be high on my list. I hate pretty much everything about those buildings given the location, including their scale and cheap construction, down to the way they change the brick mix at top--which I swear they did just out of spite for when they were forced to change it from two to three stories:
Every time people complain about one of the new apartment buildings not being the best design, I think to myself it could be worse. Specifically, it could be Portal Place Apartments in Oakland:
That's a 2012 building! Sheesh.
Speaking of which, 5637 Forbes was a huge disappointment to me. It was supposed to look like this:
It ended up looking like this:
Not perhaps the worst, and certainly not the most prominent, loser of a building, but it is right across from our school so it pokes me in the eye every day.