My thinking is that by renting to a residential care facility I can effectively utilize all the space, earn above market rent, and help provide a needed service, while avoiding tenant parking jams. 

But effective?  

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?

What effects would you expect to see from this legislation change?

Does it still provide effective results?

Particularly for your first few properties, I'd highly recommend that you manage the property yourself (if possible), but that's usually only possible (or most effective) if you live near the property or visit it frequently.

Most STR markets have seasonality, and there are untold issues in the future that will effect cashflow. 

https://logicalpm.com/new-michigan-section-8-laws-what-can-l...As the article points out, these sorts of laws often result in the opposite of the intended effect! 

For RE owners, death allows you to pass assets to your heirs and step up in basis, effectively eliminating recapture.

From experience, finding a knowledgeable accountant is key for handling taxes effectively, especially when splitting expenses, claiming deductions, and managing depreciation.