My goal is to help this family the best way I can so I’m seeking your recommendations to overcome this hurdle.  

I think the 9% Cap cash flow gets me over the hurdle of potentially slow or no appreciation but I need to be confident that if I sell during a down market, the property will not sell for less than what I pay for. 

I know the upfront cost would be a big hurdle, but the return could be very great.  

Where this would be an issue is if the showings were "unreasonable".

We would love to hear a breakdown of your acquisition strategy and any hurdles you hit along the way.

The longer you can get them do amortize the loan out for, the better your cash flow will be.And, to me, the biggest hurdle in growing your investing is the amount of cash flow you have.

To clarify, I am happy being on the note and have his input as an investor, but just need to get over the downpayment hurdle --  That's why I was thinking a commercial loan if that makes sense?

This removes one social hurdle to huge price appreciation impacting long term owners.- prop-13 property tax cap (2% rise per year) incentive to long term hold.- maintenance expenses are lower due to moderate weather on coasts. insurance cost  tends to reflect this too.- huge density of high earners and billionaires  in costal metros increases demand. - high construction cost due to earthquakes and local regulations keep supply and density of housing low.- loans esp. jumbo,commercial, and HML are cheaper in CA due to competition (3% 5yARM w/25y amortization in hot metros matching the low 2-3% cap rates!)

They are completely separate skill sets and usually have completely separate legal hurdles to jump.Setting up the phases for financing and your exit strategy will be paramount. 

It also means getting over the hurdle posed by Wis.