.- Insurance Requirement: Flood zones still matter for federal regulations.

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).

Airbnb properties can be hit or miss depending on location, seasonality, and regulations.

Think about it, was it harder or easier to plumb a house with cast iron or galvanized piping or Pex.

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

However I did note that houses are mostly really old, e.g. 100 years or older... any idea if this poses challenges in things like lead paint presence, outdated wiring, rusty plumbing, etc., or have many of the homes already been updated?   

Owner occuppied loans regualted in every state .. must have state license and NMLS registration.NON owner occ loans on 1 to 4 units are regulated same way in about 15 statesin the other states they are unregulated.Keep in mind though investor loans do not follow the same rules as owner occ and rates can change charges can change closing dates can be blown through etc

Just expressing timeline as I best understand it.Contract Jan 2022Lot Purchase Feb 2022Completed permit package submitted to city June 2022.Construction permit approved by city August 2022.Alt Seawall permit approved by city September 2022.Closed on financing September 2022.Lot scraped November 2022.Fill dirt brought in December 2022.Status update of "Ready for underground plumbing" from builder February 1, 2023.According to city portal, "Notice of Commencement" not completed at the time of this post, no indication of underground plumbing at time of this post (April 1, 2023).  

Follow your state regulations on notices but do everything you can to avoid an eviction.

Definitions:Full GutFull demo and clear out down to the studsReframe PropertyCompletely New Mechanics (HVAC, Electric, Plumbing)New WindowsFull drywall and paintNew KitchenRedo Existing bathroom and likely add a full bath in basement and/or ½ bath on 1st floor (comp dependent)Finish basementReplace flat roofNew Flooring down to subfloorsBreak, Flatten, Pour new Basement concreteThis assumes no underpinning or structure is needed.