The city operates on a block-by-block basis, and understanding those nuances takes legwork—or working with someone who truly knows the area.

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).

Quote from @Christina Hall: Sorry I only read a fraction of what you just posted … bc damn … lots of unnecessary commentary But I do understand Search volume managing hundreds of thousands of dollars per year in google ad spend and seo for major organizations If the volume isn’t high enough than you aren’t going to get meaningful traffic to drive conversionsIf there are 20 people searching per month and 10 convert and they are qualified and that’s all you need then great But the fact that you are screenshotting hundreds of form submissions is suspect and misleading to those who don’t understand hence the reason why I’d love too see your GA Good luck out there Humor me for a second.You come to the forums asking for help on lead generation because obviously, you are not very good at it, hence asking for help.

In that case, using about two-thirds of the HELOC to acquire a multifamily property—perhaps around 10 units max—while ensuring a solid team of contractors and a strong market would be key.I feel that buying just a couple of single-family homes would generate minimal cash flow, making scalability painfully slow.

If you would really like to explore the sector : why not go and message 10 to 20 operators and offer to look after their property or clean their property for a month in exchange for their knowledge and details on the numbers.

Still trying to get through some sales to generate cash.

Have you taken the time to search AirBNB and VRBO in those specific areas to see how many STRs are operating?

We'd love to escape the cold Dutch winters and enjoy a warmer climate.When we're not using the property, we plan to rent it out as an Airbnb to generate passive income.

You may want to read up on wholesaling as a way to generate some capital.

I was just on their website looking at the permit process:CityofSac-STR PermitLooks like 90 days max until you get a conditional use permit but still reading as it seems a little unclear:A short-term vacation rental may operate from a location that is not the operator's primary residence for a total of 90 days in a calendar year.