I am not a ham but my situation is quite the same here. I live in a 3-story apt. building. I just went up there and deployed a d130j scanner antenna at first in 2008 without asking. Later, up went a 45' wire for HF/SWL. The apt. managers never said a word all those years. When the present owner first showed up to look at the building, I caught him in the hall and told him about what I already had up there and asked for his blessing to keep antennas up there. He went outside and looked up at them and said "sure, they look fine". Now, I have a d130j and a Wellbrook loop both on 10' masts, and a 100' "lazy-L" endfed wire too. The building manager running it now isn't thrilled but he knows I already hit up the owner's approval so he leaves it be.
My moral here is, if you have access to the roof, just try deploying a stealthy wire without asking. The worst they can do is make you remove it. But on the other hand you might get lucky like me and they may not even trip!
BTW I'm in uptight, anal San Francisco
