It has some updates: windows, exterior paint, plumbing.

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).

Typical renovations include:Cosmetic Updates: Painting, flooring, kitchen and bathroom upgrades, and landscaping.Structural Repairs: Fixing any underlying issues such as foundation repairs, plumbing, or electrical updates.Efficiency Improvements: Adding energy-efficient windows, new HVAC systems, and better insulation to increase the property's overall value.The goal of the rehab phase is to increase the property’s market value while making it an attractive place for tenants.

No window air conditioners or freezers are ever included in the lease. 

Improvements that DON’T drive the ARV as much: Windows, Landscaping, Driveway, Rough Plumbing & ElectricalI agree with @Jaron Walling about meeting the appraiser at the property and providing documentation.

This is a penalty window where selling or refinancing out of the loan would cost you 1,2,3,4, or 5% of the amount you owe on the property as a penalty fee.

It is naturally insulated and it captures passive heat with strategically placed windows.

Then it's simple, build the home, find crews to do the work (you should already have them basically from the prior step), excavation, concrete, sealing, framing, roof/gutters/siding, windows, insulation drywall, plumbing, HVAC, electrical, finishes, etc. basically in that order.

If you want to do it yourself, be ready to answer text messages at 3 AM, solve problems within a 2 hour window, deal with contractors who aren’t able to “turn” a vacancy quick enough, and guests who want “instant” gratification.  

Windows/Doors coming next week.