Suggestions?  

Which makes me wonder if this deal either A.

If you're targeting Section 8 tenants in Chicago, I'd suggest listing at the fair market rent of $2000.

I am open to hear any suggestion or advice to make better investment decisions and get more tax benefits like setting up an LLC .

You should learn how to analyze property to ensure it's going to pay for itself.A couple suggestions:1.

Exactly what Chris suggests - buy the house from them and rent it back to them.

Hi Jeff, as everyone has mentioned, I would suggest house-hacking a 2-4 unit if you have the means.

Experts suggest this may be wise for businesses with simpler structures to avoid future headaches.2.

That is where I suggest starting as I've had some success.

I'm just wondering where this confidence comes that you are right, when last December you had just finished your first year in STR's and made $75k and was asking questions about how Airbnb places a property on the first page of search. and a year later you feel yourself to be an expert that knows more than anyone else?