I don't miss my old 3rd floor, top floor apartment in an old brick building with a black roof and no AC in Boston. I put up with that for a decade before I upgraded.
I'm ready to upgrade, as soon as I know what city I'll be moving/staying to, after new job/startup search (and what my budget will be).
It's not going to be terribly windy in Boston... There are places that sell/rent temporary roof coverings, mainly for protecting from storm damage until it can get fixed. But anyway, white/reflective coverings are available, and can be held down with a few bricks for a week.