Whenever your insurance company gave you the money, they gave you the amount of damage that has sustained, that basically replacement cost of the damage. 

Property must be sustainable at a 75% occupancy rate.  

I am going to look into roof I think as I get more rentals I need to have options to scale because picking up rent checks just will not be sustainable for me.

The property must be able to self sustain if it's a 3-4 unit regardless of the borrower's qualifications.  

Given the sustained momentum and growth of renter households vs. owner households (JCHS Data), one might say that you are actually arriving at just the right time!

They are not able to sustain a consistent organic flow of work for one reason or another.

That said, the projection still looks sustainable as foreign cash investors continue to value this area; add to that new investors from northern states with high tax burdens, and this continues to be a great real estate market. 

However, I could not sustain that long term just because my objectives are to make some side cash as I get some experience as well in relation to my time availability.

Something that can pay for itself in the long run and sustain keeping a unit open for yourselves?

This just can't be sustained for any length of time..