I ended up accessing two roofs. I started by wandering around the city looking for, well, roof access. After half an hour, I wandered into the lobby of a hotel by the harbor and tried to take the elevator the the restaurant on the 15th floor.
The elevator wouldn't go to 15, so I got off at 14 and tried the staircase. Actual process of accessing the roof documented below.
On my way home, I figured I might as well look for another, easy roof to access. I found this tourist/shopping/pavilion at Harbor Place that seemed easy enough to climb. I even got some help from the PO-lice.
More detail below.