I would like some input on how to achieve this or overcome this barrier. 

Keep focused on your goals, and push forward always to overcome obstacles.  

Data is crucial and since the original posting was about overcoming objections from buyers, i think being able to show a study that helps a buyer visualize why Zillow is a data source and not a decision making source, would be very valuable.

I know somebody who's reading this will either have been in this position and overcome it, or will have an idea of how I can overcome it.

A good loan person can over come this but it on barrier.3) TK are embarrassed to post on the forums where the culture is filled with people who a busting their butt to make deals happen.

I will find a way to overcome the limitations to financing; there will always be great deals out there, and depending on how you view the market and our economic health; there will be another major buying opportunity showing up before you know it....

I would really mess up, lose money and fail.How did I overcome these?

What  I wanted to point out by asking you why you have a partner was to point out that it is not impossible to buy, hold or otherwise have high priced properties but that the San Francisco Bay Area Market does pose some challenges to the start up real estate investorand one may think along the lines of partnering with others in order to overcome the challenges.

You have to be very disciplined (and you may be, sounds like you are) for this to pay off for the average person.         5) Ultimately, you seem to be expressing concern over cashflow due to vacancies, however with cash in hand, you can overcome those, I'm assuming, with your W2 income, margin options and other assets as you have described. 

It's just an obstacle that successful people overcome.