New STR investor in Chicago

[Jim Ostler]

Hey,

I'm Jim.  I'm 31 and work in data and analysis at an advertising agency.  I'm new-ish to the real estate investment game.  I live on the north side of Chicago with my wife and son.

I've been diving into strategies around innovative short-term rental investing (airbnb, VRBO) and trying to investigate whether a lease-ro-STR model can work in Chicago. Running the numbers on STRs in Chicago, it seems like there is an opportunity to generate strong cashflow with minimal upfront investment by using this strategy, but I'm curious if anyone has on-the-ground experience with this type of model.

Given all the red tape from HOAs and the general unwillingness of the average landlord to agree to a sublet clause in a lease, I'm particularly interested if anyone in the Chicagoland area (or any other metro really) has experience finding amenable landlords or owners who would be open to this type of rental agreement.

Thanks for reading!  Have a nice day.

-Jim