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).

Source , but for the ones that are that could be a risk if Trump and DOGE's plans to cut those jobs ends up reducing a significant amount of the jobs in DC.

Although it is possible to do everything 100% remote, most people I know who are self managing do come on site for a few days or weeks to meet and sort of interview the team they are building.You will need trusted cleaners, handymen, and also good recs for trades i.e. roof, plumbing, HVAC, etc.If you need home setup in most markets there are designers who will handle the whole set up for you, and I would want to interview them as well.  

Depreciation begins once the property is rented.It’s essential to consult with a real estate attorney to ensure compliance with local laws and to handle legal complexities.

That said, I'm using Aptly to handle work orders, and I like it so far.

Focus on key areas first (like floors, walls, kitchen, or bathroom), which may help you handle the costs more gradually, even if it means moving in furniture or updating fixtures down the line.Also, since the tenant left it in rough shape, be sure to document all the damage (photos, receipts) in case you decide to pursue reimbursement through their security deposit or in court.

Here’s how to handle those:•Negotiate inspection costs into your deal—in some cases, sellers will cover them.

People are more willing to compromise when they see you’re being fair.Know When to Get Legal Help: If she pushes back, don’t try to handle it alone.

It is to get you to reduce the amount of time you waste looking at deals and knowing what is good and what isn't good for a deal.You'll also need to know the area comps, are people putting in wood flooring or LVP etc.

So they often will reduce the leverage of the loan (getting 65% instead of 75%) or deny it (which isn't as likely).