Equipments beside espresso machine, furnitures, insurance, utilities, product cost, labor cost, taxes.

So, her and her children are living at the home and the guy is in another state with his job. 

The back deck looks very appealing, how about some furniture and a fire pit with some cool Adirondack chairs? 

My plan is to acquire a portfolio of buy and hold properties sufficient to support my husband and me in our retirement (~20 yrs from now), as well as to create a legacy for our children.

@Julian Dover Weather is not a problem in Chicago if children are not involved.

Most people with school aged children put house hunting on the back burner during these months.

Typically, I believe if she didn’t actually adopt you that that the property, as per state inheritance laws, would go to her siblings, if she has no other children, and no spouse.  

@Susan O.It could be done, but the transfer in the father's share of ownership would be considered a gift and he would have to pay taxes on the gift.Also, non-married people buying a property together like a father/daughter would lose the capital gains exemption.This is to prevent people from adding their children to dodge estate taxes.

I've seen a couple of properties in Springfield especially with a sign from the county, something along the lines of "this property is an environmental hazard due to lead, unsafe for human occupancy, especially for children under the age of 6 and pregnant women..."

We could be risking not having ownership of the house in the future but she also has 2 children with me so I would have her keep the multi if we split up anyways...... is this a bad idea?