So long story short we have a traveling nurse staying at our rental that got some water damage when the roof was being replaced, they don't have renter's insurance (which we require in the renter's agreement they sign), water damage has been remedied and is cosmetically minimally affected and still very much in a liveable state.

If want more full service with good tools and minimal fees check out Fulton Grace or Exp both popular with investors.

What we do require is a signed pet agreement that has minimal rules(pick up the crap, flea & tick prevention, etc) and we require that they send a copy of current vaccination records and a picture of the dog(s). 

After analyzing GIS data, I discovered that my neighbor’s house, garage, and shop are built with minimal permissible setbacks (50 feet to an inch) from the boundary line.

Based on rental income would be great since I'm self employed so minimal documentation is best for me. 

You are minimizing your input to maximize your output (output being an appreciating asset, paying down principal, tax benefits.2.

After we move in 4-5 years, I would rent out both units.Pros:Potential for long-term appreciation in San Diego.Cons:The property will not cash flow enough to cover the mortgage while we are living there.After we move, it would provide very low returns and minimal cash flow.Would require a significant portion of my liquidity, making it harder to invest elsewhere and grow my rental portfolio.2.

I have minimized that risk by being very strict in my underwriting. 

Working with a title company and consulting a real estate attorney can help minimize exposure.

Vacancy/turnover is a minimal consideration.13.