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).

Both Fort Lauderdale and Pompano have fairly relaxed STR rules and regulations. 

They see a renewal of the current business tax rates, regulation and permitting rules getting slashed, tax code being simplified, and federal deficits on a one-way ticket down the elevator (which are a longterm drag on economic productivity).Just look at the growth in tax code complexity over the last 20 years.

Mounting shelves, a TV, or other large items that requires screws, bolts, or anchors should be regulated by the landlord and charged to the tenant. 

It is right on the fringe of being legal/illegal, and lawmakers have been talking about how to regulate it for years because it can be a dangerous process that leaves end Buyers feeling like they weren't represented.....especially when they see the closing statement and find out how much the wholesaler made just by getting to the Seller first. 

There good ways to navigate the market between the 5 counties, 2 states and many different HOA regulations.

That would bypass many city/state regulations that force landlords to rent to people here illegally. 

Low Down Payment OptionsGerman lenders often offer financing programs requiring only 5-10% down payments, particularly for primary residences.Strong financial regulations in Germany support these low down payment options.3.

Duplexes provide privacy, flexibility, and scalability, but strict short-term rental regulations may increase upfront costs and maintenance.

I exited the market due to the short term rental regulations - properties that are rented under 90 days are considered short term.