Also if someone is close that likes coffee would like to sit down, have a cup of mud and potentially be a mentor/ advisor.

You will definitely need a source of income to get a loan (from a traditional mortgage lender), and that income can in fact be from a job. 

In San Francisco, a "traditional" suburban driveways are rare and are often times confused with the sidewalk portion in front of the building. 

Are you using a traditional bank or a hard money lender? 

If you go the traditional route you would have to wait 6-12 months for "seasoning" before you could refinance the property and get a traditional mortgage.

Traditional loan with a local bank How did you add value to the deal?

But upon ripping it up, I found it to be soaking wet and layered with piles of dander/dirt, which due to the moisture was more of a mud -yuck.

You'll want to consult a professional money lender (hard, private, traditional, etc) about the different methods of financing this if you aren't a cash buyer.

At times I go as far as helping them create an annual plan and find local contractors to take care of the routine maintenance work.Has anyone ever run into this situation where a traditional homeowner could benefit from the way a landlord does things?

Well for a traditional home buyer they want to build a house where they  have control over things.