Members span the gamut from "mom and pops" to large professional management corporations. 

Most investors are small mom & pop investors I believe.

If the loan is not being serviced by a third party then odds of getting this are going to be slim as most mom and pops don’t know how to do this but yes they should.  

(I just went through probate when my mom passed and it sucks and would like to prevent my successors from having to deal with the same if possible).Bonus question, one of my properties is still under mortgage, he mentioned something about transferring it to an LLC can trigger a due-on-sale clause but not when transferred to a Trust.

I love how Mint was "semi-automatic", and did a decent job on its own although you needed to come in and tweak categories.All this to say, are there any other Mom & Pop investors out there with more complex personal finance that have found useful software solutions? 

If you have less money than will need to look into retail condo investing and mom and pop type stuff.

How are unsophisticated mom & pop lenders in 2nd and 3rd position on those properties going to get their investment back?

The equity market skyrocketed in margin for Nov24 by almost 10% MoM and 29% YoY. 

My tenant, a single Mom, had rented my rental for almost 2 years with her son and couple of grand children.

Section 8 wants the landlord to be penalized for not acting like the tenants mom or dad.