Some title companies will require an operating agreement, even if sole member, to buy or finance a property.  

Can you please share contacts who operate in Austin or San Antonio?

Costs will be far lower, but an owner/operator would still get the benefit of staffing and material efficiencies. - You could consider owning those as rentals and leasing out to the businesses. - You could sell the land to an owner/operator who wants to build assisted living. - You could own and operate those yourself and just hire great management or bring in a management company. 

Understanding my customer, I bought similar properties to what they were currently renting.This strategy is similar to how national retail chains operate: identify your target customers and provide what they want.

Strategic planning and phased upgrades are critical to balancing renovations with ongoing operations.

Strategic planning and phased upgrades are critical to balancing renovations with ongoing operations.

Strategic planning and phased upgrades are critical to balancing renovations with ongoing operations.

Strategic planning and phased upgrades are critical to balancing renovations with ongoing operations.

Is that the case or is it  I'm wondering if you need it to be considered a separate dwelling by the city to operate just the basement as an STR?

@Daisy RuizTo echo @Michael Baum, I have not seen or heard from many people operating STRs in Chicago.