Which size of home is typically perform best on a cost benefit analysis?

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 had one short term rental that was granted a permit earlier this year and I have been operating it for months now as an STR.

Quote from @Steve Englehart: I currently have two long term rentals and am looking into buying into the short term rental arena.  

Avery Carl's Book, 'Short-term rental, long-term wealth' How did you find this deal and how did you negotiate it?

The combination of Germany's stable economy, well-regulated property market, relatively low interest rates, and the opportunity for long-term capital appreciation make it a compelling choice for U.S.

With that said, the income can still offset the cost of holding the property as a long-term investment.

Sounds like you’re trying to google and perform your own heart surgery.  

@Yamil NafRaising $160,000 for your short-term rental (STR) venture is a great goal, and there are several ways to structure the deal to minimize your upfront costs while attracting investors.

Why do you think purchase contracts are so long and have such small print?