Well........they sent a picture of a section of the roof, some of the shingles are u and guess what- NO insurance on it now.    

Unless there's an active leak, there's no reason.

I have a strong work ethic and don't shy away from hard physical labor thanks to my granddad making me carry pack of shingles up on roofs at 6am during my summer when I was 11 years old, my pay was dinner that night lol. 

It comes with the territory like a water leak, roof damage, etc..My $0.02 ...

I am looking to cash out, so i would like to know if i should be adding more money into the rentals such as painting/roof upgrades?

This stunning home boasts New hurricane impact windows, Newer Water Heater, A/C- 2020, and Roof -2017.

If you replace them now, then hopefully less headaches going forward.For example, I had to replace a roof on one of my duplexes, so I asked the roofer for a combo deal on another duplex with an old roof to get a better deal.

If you wait 30 years to start budgeting for a roof, the house will rot into the ground from leaks before you have accumulated enough to replace it.

The time spent meeting pest inspectors, home inspectors, roof inspectors, HVAC guys, septic inspections, any contractors for work that needs done, photographers (paid by selling agent) signs and other marketing, Omissions and Errors insurance, MLS fees, NAR/CAR fees, car insurance, gas, only to have a deal fall apart over something.

However, for a rental property we may feel differently as it is an investment and not the roof over our head.