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).

This may be controversial but it seems like you would be saving a lot of money at the moment given your reduced living costs.

Proper documentation ensures you’re prepared to substantiate your claims.Federal REP or STR material participation allows you to deduct rental losses against active income, significantly reducing your tax liability.

Screening everyone over 18 helps reduce the risk of costly evictions and ensures you’re fully informed about who will be living in your property.Additionally, be mindful of the number of occupants and how it might impact your property.

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.

When this occurs, area incomes fall and cities reduce spending on police and schools.

He tells you to pay him $5,000 (or much more) to learn all the "secrets" that made him wealth, but then he doesn't tell you that his "secret" was to increase earnings, reduce expenses, save up and invest.

You could also add cash to your exchange account to reduce the debt replacement if you wanted. 

Combine those factors and start thinking of nightmare scenarios, because they are very real and you must be proactive in policing against there potential to occur. 

If I pay it off, I could maximize cash flow earlier, reducing financial stress and allowing me to focus on other ventures or simply enjoy life more.On the other hand, I know some people advocate for keeping cheap debt and using the extra cash to invest elsewhere for potentially higher returns.Why I’m leaning toward paying it off:Security: No debt = peace of mind.Financial freedom earlier: A fully paid-off rental would give me a significant monthly cash flow?