I think this building has deferred maintenance (roof leaks into the foyer when it rains, parking lot has not been striped in a while, I assume more will be found).

your issue is not one of money, its one of priorities. your tenant no longer prioritizes rent, because you have allowed your agent to deliver the message that rent does not need to come first. when the tenant knows her roof is on the line, she will let other bills fall to the side in favor of rent. 

If so, were permits pulled & were they installed by a professional5.Are any of the homes rented to students6.Is there a flat roof7.Are there asbestos The Year that the following were updated (either partially or fully) would be good to know:- Heating systems - Roof- Plumbing- electricalSome companies will not write properties with systems that have not been updated.If you are living there, the proper policy for a 1-4 family is a "Homeowners" policy.

Anything over 50 years old they require documented proof of renovations for things like roof, hvac, wiring, and plumbing.

Hope for the best, but it will be a scramble trying to get the roof dried in or other repairs immediately after the storm.  

I like this niche because it limits my risk on several major expenses - exterior and roof.

Some will mount them on the roof of a retail building and others have a post with satellite on the corner of the building that runs to the tower.We had one before my client was looking at.

Overall the house has great bones but it will take a few grand to complete the punch list of items needed to remedy: radon mitigation, surface mold in attic, slight leaks at a few easily accessible spots in the roof, electrical service work.

You probably shouldn't be ripping off shingles to replace roof decking as your first DIY job. 

Garage already has its own door entry and windows on each side with 2 solar panels on the roof.