I was conducting an extremely seasonal business and after 8 years of operation the business was insolvent. 

The properties we operate are all in Indiana. 

Im a medium sized operator - 46 units- and my typical deal has an ARV from 200 to 230 when its finished.

You could form an LLC and have the operating agreement that allows your boss to require you to purchase his membership interest (or allow you to purchase his) in a given time frame.

It's important to understand the zoning/code requirements and obtain all necessary permitting if you intend on operating your real estate as STR anywhere in the country.

It's the lenders who usually require that the property is listed under an entity, depending on the state that they operate on.

Currently, I am self managing all the operations.

CommissionerYou really need to see how this operates in the real world, and with a Tax Court Judge looking at all the facts & circumstances.  

Many local businesses that operate in the downtown area by the state park (including some famous attractions) close for the winter or reduce hours.

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).