@Kevin Tang I believe there’s currently a moratorium on issuing new STR permits there (until they determine new codes/restrictions).

One thought I had was taking a look at interesting properties and determining what price works for me.  

There are a lot of variables to determining the cost of development.. hard costs, soft costs, financing costs, holding costs, etc.

I am pretty confident in being able to determine an ARV, and I have made a bunch of offers so far and even got 2 under contract (that I backed out of due to rehab quotes being too high and numbers not working because of that).  

The town's tree warden had to come out to assess other trees along the street and determined he will be cutting down at least two of them (if these two came down, they're definitely coming onto/ into the house).Have you run into a situation like this before?

Hi @Kris Columna, the most important factors in determining whether or not you have equity are the Market Value and your current Principal Balance on your loan. 

They did their job - you determine the rent amount, not them;  they can advise you, but you make the final decision on rent amount.  

To find condos in Chicago with positive cashflow you're going to look for condos that are either listed with a realtor or For Sale By Owner and review the financials to determine if the cashflow is positive.

The most determining characteristic will be money -- how much do you have?

I would interview other agents in your area to determine if you want to become a real estate agent.