Now if the ceiling fan has a broken blade, they would get charged. 

The house has a family room (a deck that was wrapped, which is usable, but in dire condition) with an unfinished rumpus room in the basement.

The City banned decks on top of garages (although that ban has been lifted recently) I cannot see a scenario where they would let you have an apartment. 

On a composition shingle roof, you would have a flashing that is integrated into your shingles (like the roof vents you have now) below the flashing (or integrated into the flashing) is a mechanical base that connects to the structural members of your home (rafters) or the deck (plywood), dependent on the racking manufacturer.

From really just decking them out and doing completely right in the beginning.

I do not know the condition of the roof but the top floor tenant owns the rooftop deck on the roof (however, I may still be liable for roof repairs?)

Ordered similar coloured siding and stained wood shakes to install, instead of extending the roof and adding timbers on the front deck.  

The rental apt. is pretty unique (3 beds, 3 baths, 2 of which are on suites) with a private rear deck in a nice residential neighborhood, so I don't think a locked door will deter tenants. 

@Wayne Brooks @Julia Deck-RussellThis has turned out to be a major PITA! 

Less for basements that aren't finished, garages, and decks.