I have possible deal I could make happen with a friend of mine with his two flat in Chicago.

With their lease renewal coming up we'd like to include a flat rate for their Water Sewage and Garbage (WSG) portion of the utilities.

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.    

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. 

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.

I see a lot of people doing all these crazy calculations on 3 and 4 flat deals (When I started i did it too, ha). 

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

I was told they flat out said no and the student was pissed.