I would highly suggest that you tune in to the BiggerPockets Podcast and attend your local REI meetups.

I just have house rules loaded.For direct bookings I use a simple one page form with their dates and the amount paid.A hotel doesn't make you sign a lease.

By this time, I was feed up with how long it was taking (and the multiple calls to AHS) and why their vendor couldn't quickly handle a simple item.

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.

Your mentor has needs; try to meet them and develop a mutually beneficial relationship.A mentor can benefit your growth, but it's not as simple as one post on a forum full of strangers.

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 wondering if any one can give us suggestions on providing/offering health insurance.

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. 

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. 

No reason to make so much out of something so simple. 1.