@Eric Bate  based on the numbers you provided you could do a refinance and take cash out to support a down payment on a new property in Chicago.

I don't think there is any problem with retaining a life estate, but I would have a tax practitioner that specializes in Estate & Gift issues assist in making the relevant calculations and drafting the supporting documentation.

After that I was thinking I could renovate and add a wall to make a 4th bedroom. 

I am interested in building a team to support my work in this market. 

Minimalist kitchens along one wall with an island to separate the kitchen from the living area. 

The other great thing is, at anytime you can get a new appraisal and if the property can support the loan on its own the bank will release the hold on 2nd piece of collateral.

Thanks for your feed back and support, I’m currently not looking for partners but will definitely keep you in mind if things change.

That is based on the following assumptions:Rent: In-place rents are at marketVacancy rate: 10%Expense ratio: 50%Cap rate: 6.5%Loan Interest Rate: 5.25%Debt service coverage ratio: 1.2Down Payment: 20%Best practice would be to ask brokers for cap rates and market rents to support some of your assumptions. 

Sherwin-Williams eggshell on the walls and white on the trim. 

Owners do not normally remember they are in the people business.. 4 walls and roof anyone can buy...Running a profitable business model and dealing with tenant challenges is not something most new landlords think of