With 3 STR's I'm trying to start organizing and automating processes for myself.

You can find that out through local or state wide associations/organizations that support your industy (ie. commercial real estate association, state contractors organization, small business owners assoc., etc...)

The seller is an older woman in poor health conditions - currently in hospice - and her only daughter is trying to organize the whole transaction.

If it's a larger organization, feel free to inquire about their different staff qualifications.2.

It's a government organization that helps small business owners and has resources for loans.

For businesses, note the owner's address, which usually indicates the state of organization filings.

I had to do community outreach to my neighbors and my local Resident Neighborhood Organizations.

However I am learning that in order for this to be effective you need to come up as one of the first organic websites people see on Google and to get there you will need to buy ads and/or have a really good SEO site. 

Has anyone ever had luck building their own organic list?

Having a network of friends and family in the area is a big draw and having an organic familiarity with the market was a competitive advantage for us compared to other markets.