Thanks everyone, and  have a wonderful holiday weekend ahead!

Luckily, I found out I have until 3/30 to find coverage (I wondered why my regular insurance agent wasn't rushing to get me new quotes).

I have a property manager in place (one recommended by RTR) and he suggests (i) new build supply is way higher than demand (ii) realistically (if at all we find a tenant) we should target a rent of $2100 vs $2500 projected by RTR.

My suggestion would be to come out to as many in person meets as possible (https://www.biggerpockets.com/forums/521/topics/1177645-tax-...), ask tons of questions, and figure out how to hang out with people who are doing what you want to do (add value, work for free, do anything to get that experience.What area of Chicago are you looking to invest in?

Also the advice on writing offers and the lower purchase price is something I have been wondering about given that I have not yet ran preliminary deal numbers at purchase price without negative cashflow for single family rentals in my area.

Single family is really easy, multifamily is a little more complex my best suggestion is rural land at least 0.5 acres and up for easiest rezoning. 

I see a lot of houses for sale and I am wondering is it a good market?

The fact you learned the children are the ones selling the property through a neighbor and this was not clear in the sales agreement suggests the proper authority might not have even existed to execute the agreement on behalf of the estate in the first place. 

I am willing to learn as much as possible so please suggest materials and conferencesThank you

I was reading the book "Real Estate by the numbers", the part on EV, and I was wondering on how to calculate the EV when I do not know the probabilities/percentages of each outcome happening, can you give me an example on EV with a rental unit please?