A couple of thoughts:The best quote I recently received for a roof (1,700 square foot ranch - SF BayArea) was about double that of your budget item;  the electrical line item also seems low based on charges I am seeing up here ($100/hr -$120/hr) and what I understand will need to be done (essentially wiring an entire house)

New roof, upgraded electrical, plumbing, etc.

The reality is your entire portfolio shouldn't go vacant all at once, or need new roofs all at once. 

Dom, for the money (typically $250 to $300) you can't go wrong, they should tell you the age of the roof, the age of the air conditioning unit and any electrical or plumbing issue. 

My capex budget includes roof 25 year life span, appliances and hot water heater 12 year, hvac 20 year life span , bath and kitchen remodel 20 year life span, etc. i use 10%. 

(also the algae or whatever on the roof looks grungy, I'd fix that if possible)Good Luck!

We just found out we’re going to have to potentially renew the roof.

By the time you hit 12 years, you will be out of pocket for at least one (or 2) roof, 2 kitchens, 4 paint jobs, 2 new floors, driveway, and other misc items that will add up. 

I just purchased a property off of Hixson Pike and what I originally thought was a French drain issue has now evolve to need some excavating along the back and side of my new property.

as long as you have funds to keep the lights on and feed your family.Stocks are great 5, 10, 20 years from now , but they don't give you a roof over your head.