You aren't going to take someone to small claims court for damaged paint or anything, and if a major loss occurs the tenants are almost never collectable anyways. 

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?

Step inside to discover a freshly painted interior complemented by newer flooring, fixtures, and appliances, creating a coastal ambiance throughout How did you finance this deal?

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Couldn't pass the inspection until he ripped it all apart, removed 2 new kitchens and 2 new bathrooms, moved walls, etc. and made it a 2-family building.

I would definitely recommend spending most of the money in renovations on the kitchen, bathroom, and exterior (siding, paint, landscape). 

Oh, do you think you can paint the walls before I move in?

Fix the cabinets , paint them white ( Sherwin williams gallery is an great cabinet paint ) . 

I can definitely say that while the bigger fire we had was a pain... it actually worked out really well... in the end we had a much improved property, and we stepped in and did as much of the work we could do ourselves that the insurance company was compensating us at  'retail' rates for... like painting, and replacing cabinets, and other simple tasks.  

Renovation, renovated the kitchen, bedrooms by adding closet doors, LVP flooring through the house, new paint.