@Kyle Kulhanek To retitle your Chicago condo into an LLC for liability protection, start by forming the LLC with a clear operating agreement outlining ownership and responsibilities.

If you were renting to an only a couple as a long term tenant and they beat each other up (domestic violence) your liability is minimal.  

Subject to tax liability on the gains of course, but it gives you more flexibility.  

This way the buyer doesn't feel like an added cost is unexpected and at fault of the seller who is turning over the property to them with potential liability.

- Controlling costs for payroll processing, unemployment charges, workman's comp and liability insurance- Coordinating ServiceTech & tenant schedules for appointments--- There are several industry vendors that focus on just this!

There is extra costs, more regulation, and more liability. 

I think there are liability issues with putting some kind of booze out.

You'll want to put together a personal financial statement (basically lists of all your assets and liabilities) and have your tax returns ready.

Make sure you have that addressed just from a liability standpoint. 4) You could also look into a mid-term rental option with traveling nurses if you think the unit is truly rentable. 5) AirBnB restrictions have gotten much stricter as well in general in Chicago, so make sure you are on the right side of those if you put your unit up since you are required to register with the City.

As I got older and accumulated more I scaled back on RE due to the work and liability.