., your good deal may be priced at $80/sqft "all-in" in the submarket where retail houses are priced at $110/sqft and rents are above $1/sqft.You need to know these numbers before looking at individual properties.

While I am familiar with the ADA response to this topic -essentially all favorable to a tenant, but it appears there is an abuse of the definition as they are all employed, functional individuals who leave the assistive pet at home all day.

It would also be hard to effectively make offers without doing the math first, so I think the method would be counter productive.

Followed those up with some motivational/self help reads that aren’t focused on REI and now I’m onto more real estate specific like Long Distance REI and The Book on Rental Property Investing.

Then personalizing an individuals RE short term rental data with functionality tools similar to what AirDNA and Mashvisor have.

When you say, "track each property within its own class for accounting purposes," I assume you mean, can you track properties individually or only grouped together?  

Is there a possibility that it can be sold out seperately as a individual units later?

The key is to find really motivated sellers.

An individual helper could possibly help you keep organized depending on their skills. 

This is entirely going to depend on their individual lending criteria, no general answer is going to do it.