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).

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

@Parker BullardFrom my experience, house hacking is a great way to reduce housing costs by renting out part of a property, like a duplex or triplex.

But I’d also buy the $200 5 year warranty.My last/only stackable I bought last year was LG, the combined towers to try to reduce noise, increase ease of use, and presents higher end look.

You'll likely also reduce your cost of living by moving to a stabilized apartment.Depending on the cashflow and debt paydown, you can use this strategy until you've built enough equity to reinvest.On the other hand, getting into a multi-family after refinancing will also help you build substantial equity to rinse and repeat in the coming years.

If you’re considering Section 8, some cities (like Detroit) have high demand, which can reduce vacancy risk.3.

During that time, you will have no vacancies and little maintenance costs, and the resident will provide the $$$ to reduce your principal. 

A 1031 exchange doesn’t apply, but funding through a self-directed IRA can defer taxes, though profits from debt financing may trigger UBIT.To reduce taxes, consider forming an LLC for better expense deductions, offsetting gains with investment losses, or holding the property for 12+ months to qualify for lower long-term capital gains rates.This post does not create a CPA-Client relationship.

If you constantly cash-out refi you reduce equity and cash flow.

Now that it’s a rental, you can deduct mortgage interest, property taxes, insurance, repairs, maintenance, and depreciation to reduce taxable income, but depreciation will be recaptured at up to 25% if you sell.