All of the normal methods don't seem to produce much return for my dad, and even if he got 100% of the cash flow it would take 7+ years for me to see any profit.

I am concerned that it appears you are considering renting to someone you have known many years.

We are pre-boom and it is more valuable to have the property than be too concerned with Cash Flow.

My only concern is getting approved "multiple mortgages".

Other concern is we are continuing working on adding more properties to the portfolio so within 5 years we could have 5-10 more properties.

My concern with including closing costs in the Cap Rate is that you're often paying points which ties into Levered CF.

Are the bigger dogs not concerned with newbies and their “no money what to do posts”?

Is  this something that I should be concerned about in California?

I'm not concerned about the companies being able to pay as they are very large and profitable. 

Our plan is to move forward initially with buying single family homes in the Chicagoland area, and then use the BRRRR method to raise the equity in them so that we can grow larger and larger by buying properties with the increased equity seen after each renovation.