They are all under a single roof and currently rented out.

i.e. deductible for a roof replacement or replacing an HVAC unit or replacing a hot water heater? 

The area wasn’t heavily affected... but a tree on the property was uprooted and unfortunately knocked down part of the home (roof and foundation were affected). 

The inspector checks the plumbing and electrical systems, the roof, the foundation, the HVAC system, and the general structural condition.

Engage professionals to inspect major components such as the roof, plumbing (including sewer lines), foundation, drainage, electrical systems, HVAC, chillers, boilers, termites, exterior walls, balconies, stairs, rails, and concrete.

I want to do the project for the long term hold and cash flow aspect.

Your mechanicals and capital expenditures are a lot more important and more expensive to fix than a pretty kitchen. its better to live in outdated kitchen and have a well kept home with updated mechanicals/roof/hvac than one that looks pretty but will start to crumble5.

So I hired a company to pressure wash my apartments (8 units) in New York State and the guy fell off the roof.   

Kill 2 birds with 1 check, reinvigorating areas and creating the growth and expansion that feeds not only housing needs but with all the ancillary things one needs to have along with a roof over the head. 

She can make a decent paycheck while learning all aspects of property management quickly.