It’s great to see a fellow professional diving into the investment side of real estate—it’s such a rewarding journey.

There are a lot of good people in Dallas and very experienced professionals in all services you will need. 

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).

I will say the abatement if you do it right with a good contractor will be pricy since they have to abide by some different regulations on disposing of it. 

They will get the highest price and the best terms for their property by marketing it professionally and exposing it to the maximum number of retail buyers, which means putting it on the MLS with an agent.

I love the flexibility they offer for traveling professionals, military families, or folks in between moves.My main questions:Have you noticed increased demand for midterm rentals in this area, particularly from military personnel at nearby bases or healthcare workers at local hospitals?

Hi Tio, I don't think hiring a professional designer is wise as it will cut into your margins and sounds like you have a tight budget. 

I'm currently a leasing professional at a luxury high rise complex in downtown Ann Arbor.

I think Landlords are better off using strong policies, knowing the law, acting quickly and professionally.

Unless you qualify as a Real Estate Professional (which has strict requirements), your rental losses can only offset passive income.