Hey Barredo, I would target the PR/Executor (or petitioner if that's the given title of the estate administrator).

It will be an administrative nightmare a soon as the number of transactions increases (i.e., more properties). 

Simply work with the Section 8 program administrator in your area for a smooth transition. 

Administratively speaking, pros, cons, rent delivery times, ease of ensuring payments are pointed to the correct receiving account etc?

I use Chicago Trust Administration Services - Steven Miszkowicz.  

I don't want to discount anyone on their views or information on schools as it's not one of my focuses, but I would like to note that good schools are dependent on good teachers, good administration, and a supportive (or non-intrusive) city council. 

If you complete enough sales to cover their risk (insurance etc) and administration overhead, you could probably stay there a long time. 

@Bill HenleyAs long as the borrower is not a disqualified party (below are some examples), investing in notes via a self-directed IRA is a popular alternative investment type.YouYour SpouseYour natural parents and/or your adoptive parentsYour natural grandparentsYour natural children and/or your adopted childrenThe spouses of your natural childrenAny fiduciary of your IRAAny people providing services to your IRA–such as your IRA custodian Your IRA administrator

Yes, brokers do hire assistants, but that also means you will be working for that broker at least part-time handling a myriad of administrative tasks.

I would add to that, that with the new administration, things can change pretty quickly, including in the affordable housing arena.