How many coats do they think it will need?

If the hardwood in the laundry area is in decent shape, I would just "screen sand" it and apply a couple of coats of WaterLox clear finish.

Floors need refinishing, carpet needs replacing, fresh coat of paint, couple spots in roof leak on the exterior (possibly flashing needs replacing in 2 spots).Sellers is in pre-foreclosure and just wants out without going into BK.  

These are valuable experience getting shared here... definitely give me lots of food for thoughts as I try to venture into commercial after 10 years in residential.... totally different animals as I come to realize

A painter is going to charge you ~500/coat on the cabinets.  

Do you have any animals?

Combine that with some YouTube videos and there won't be much you can't accomplish by yourself (depending on your level of skill for swinging a hammer).You can pretty much count on new flooring, fresh coat of paint inside and out, new lighting, and remodeled / updated kitchens and bathrooms.

My first property is in MA (3-family where I live currently) and I'm quite familiar with everything here but RI is a different animal.  

I grew up in Des Moines but I live in Denver, Co at the moment.  

Owners trying to rehab themselves often don't know little tricks such as adding a spoonful of dish soap to their mud to help eliminate air bubbles (and thereby, an additional coat), or that the process of coalescence in exterior paint is negatively affected by an ambient and/ or surface temperature below 50 degrees.Being from Cleveland, unfortunately I can't much help with the Milwaukee area.