Looking ahead, have a knowledgeable mentor, investor or inspector look at some of these properties, ideally with you in person.  

Hi Lisa - I am far from an expert on CA, but on the income I personally have a premium AirDNA subscription and start there. 

We held an in-person meeting over 6 months into the project to express our concerns with the timeline and to request weekly check-in calls.

If you asked the average person outside of New York State where Upstate NY is, the most common answer would be "north of NYC."

I always got a DP3 policy with $500K in liability coverage on my SF rentals.If grandpa is living in your place, his personal items are not covered.

You also did not give them any firm instructions about how to handle this.

Given these factors, should I consider renting to this person? 

As a landlord who likes to have control - this doesn't work for me personally.  

Like @Brian Burke said there are many different ways cash flow can be handled and waterfalls structured.To keep the same example but for a 9% cash on cash return:$100,000 starting capital account balance$8,000 preferred return accrual (return on capital)$1,000 excess cash (return of capital)($9,000) total distribution (preferred return distribution+excess cash)$99,000 ending capital account balance

I still flip and network in SJ, personally I'd want to have a experienced real estate attorney for an eviction.