You're definitely not alone—several Chicago landlords have reported similar issues after getting new meters installed.

No landlord is going to want to repaint a rental.

Basically any cashflow is for maintenance for about 5 years .Any thoughts from experienced landlords?

By house hacking It lets you get in the game with minimal money down (3-5%), while also covering your mortgage and gaining real-world landlord experience.

It sounds like you have actually really enjoyed the landlord process which is not always typical, but I am curious...would you rather spend more time with your family or spend your time figuring out how to make more money vs. managing the properties?

We are the owner and landlord of the properties, not the operators.

If you're a small mom and pop landlord it's best to go DIY to learn the ropes and if you scale beyond 10 rentals then maybe hire a PM later, but at least you'll "really know" the ins and outs (only if you go DIY 1st).Tell me.

A lot of BP Pro Members are landlords so they need a software to manage those properties, so the RentRedi Perk saves members around $360 in software costs. 

Is it a landlord friendly city and state ? 

Replacing roof, repainting house, minor landlord scaping for a multi family is not going to see a major jump in ARV.