Also, what are your financial objectives for the investment (term, rate of return, size, etc.)?

That's just the realities of the Southern California market.I'm not gonna call people who buy out here where I live crazy, as everybody has their own goals, but people are certainly not buying with cash flow as their primary objective.  

Your cash flow is not a given.I would back up and ask yourself what is your objective. 

I don’t think he will object to it because I’m sure he is not enjoying these discussions either.

With wholesaling its about marketing and sales....overcome objections....solve problems...negotiate wholesale prices....control the property....assign/double close...repeatThere are other exit strategies too 

The majority of people don't have the courage to see themselves objectively and vulnerably as you are doing.

It’s a very big industry with lots of options and it’s easy to get shiny object syndrome and then end up in paralysis by analysis.

Look for objective signs.

@Benjamin Amaral  windshield damage and other falling objects like trees are normally covered under comprehensive. 

I have 2 SFRs and the objective is to use this software for rent collection, lease management, marketing for tenants, property maintenance, accounting etc.