Apparently, the person I am under contract with was managing the estate of the actual owner who recently died.  

Probably not a good person to hire, maybe let your bosses know. 

I am really interested in meeting any in-person groups in Boston (now-May) and Chicago (September-Onwards).

I personally wouldn't buy an old home as a rental, I only buy 1980 or newer for myself, all of my properties are in the north part of Gilbert built between 1985-2003.

I know this is a differing topic on the forums, and online in general, but having the legal background/education and knowing estate planning concepts you'll realize it shouldn't be.  

Personally, I self manage but have built systems to allow it to be fully remote and very passive.

I personally would recommend the last method.

I've got stories that would be hard to believe on some of my seller financing deals, contract on a napkin, personal check for a notarized deed, hand shake deals, etc., etc. and a LOT of fun.

I mean I got financially wiped out personally..

Insurance- personal property.