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.

I think that goes a lot to show you how engaged Tardus clients are. 

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

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

Implement scalable systems and processes to effectively manage and grow your real estate holdings.

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?

The main criteria to evaluate this is when did you complete the start-up phase and became actively engaged in business?

While traditional security deposits have been the standard for decades, they’re not always the most effective or tenant-friendly option.

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, I bet-ya it's also effective.