Starting with a 10% deficit could be a significant setback, especially if the fair market rent is higher than what you are currently charging.

Most of our clients are missing part of "TIE" equation, so they pay us to manage.Another thought, but you'll need following along with me:  A $2000 per month deficit might not be that bad, depending on what you paid.

States and localities are severely limited, for the most part, in their ability to run deficits, since they cannot print money, and that has constrained most over the top spending.

Your numbers show a deficit of $1700.

With the CARES ACT passed and in full effect our national deficit is looking to hit 30 Trillion Dollars in the near future!

I don't think it's likely that the midterm rental market disappears or Chicago lawmakers find a way to outlaw it but this helps to ensure you don't operate at a deficit. 

It looks like the owner is going to be in deficit. 

I’m also afraid of all the possible new taxes that could be imposed to try to fight this insane deficits/debt we’re running up.

Lucky for us, the LTR rents are higher than in previous years and can make up the deficit from the paused STRs.

Even if the bank lends on projected cash flow, you are at a deficit if Code requires closets that you do not have.