Typically 75% of rental income can be applied towards your DTI for qualification. 

I am working toward passive income to live off of.

Over time I have amassed a good quantity of houses with no mortgages.

The city where you invest determines all long-term income characteristics.

Jimmy,You need to show (2) years of 1099 SE income in order to use FHA, or traditional financing to get approved for a mortgage.

Vanessa, If you choose the seller financed route, you could potentially continue investing under the bank's stringent debt-to-income radar, so to speak.

Obtaining the type/quantity of land we would like to settle on at this point in our lives is not really feasible (i.e. several thousand acre cattle ranch).

If you're interested in seeing how that all breaks down from an income and expense standpoint, I created this Sankey diagram to share with you:As for me, I'm planning to leave my w-2 job and take a little career break before deciding what's next for me. 

Virtually everyone lives somewhere especially true for those that pay taxes (in CA property and income tax).  

—to help you succeed.Quality over quantity wins every time.