Those properties have very specific details, guidelines, and rules that are different than Indiana and I understand well how it works. 

Short Picture: Instead of dumping 300K out of a brokerage account all at once, how about you find another investment you are comfortable with, multifamily specifically, and only withdraw the needed funds for the down payment on it from your brokerage account. 

But your can't go wrong with either.

Some things that went wrong were rather unpredictable, like an improperly buried wire for a sewer pump that the ground and hot wires began touching throwing the breaker.

Does anyone have recommendations for good, reasonably priced countertop installers/fabricators who do work in the north/northwest suburbs of Chicago, specifically around Prospect Heights?

If your brother is looking to invest in real estate largely from a tax reduction standpoint they should pay a qualified real estate tax strategist to review their specific situation and what may or may not work for them. 

Most get cornered into purchasing specific property types because its what their resources allow.

My biggest concern is just having boots on the ground in case something goes wrong.   

Use forums to ask specific questions and listen to BiggerPockets podcasts from the past couple of years.

I think coaching can be really helpful if it's specific.