However, due to a leak that impacted the kitchen, I had to demo some of the drywall and a small part of the ceiling.

(New Kitchen, Bathroom, Flooring, etc.)I look forward to hearing back from you all,Vincent Cavalieri

This would take a decent amount of investment to improve the kitchen and bathrooms.

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).

Fully stocked kitchen.

Nice wood floors but ugly kitchen and baths.  

Purchase price: $645,000 Cash invested: $60,000 Two Unit property with lots of living space3000 sqftOne parking spotBrand new kitchen addedW/D in both unitsGood for Long term / Mid Term / Short Term What made you interested in investing in this type of deal?

It is in good condition, nicely decorated, top notch bedding and well appointed kitchen with a large lanai and no pool. 

I would assume that there are sound proofing updates that you would be able to do such as windows, walls, etc.

Replacing windows went up about $100 each just to play by the rules.