I enjoy how you lay out real numbers. A lot of people wouldn’t do that. While you admit that you are somewhat conservative, I think the $1M in CD’s is just too conservative. Assuming you don’t need the cash flow now (which you say you just save anyways) then all that could be invested for potentially higher returns. For example, what if you bought San Francisco real estate along the way instead of CD’s. Or, an SP500 Index fund. I bet your average return would have been higher than 3.75%. Sure you could lose it, but the point is if you don’t need the cash flow now, you should try to increase that nut as high as possible until the day you actually need it. Your nut could be $5M right now if you had invested in asset classes other than CD’s for the last 14 years. Don’t get me wrong, you have done far better than me, but I guess I would take a little more risk if you don’t rely on that cash flow.
I’ve built several businesses since 2008 using one or more of these models. I’ve been featured in magazines and articles across the globe, and since I started my journey I’ve generated over $5M in earnings from these businesses. All of my income and expenses for those businesses dating back to October 2008 have been tracked publicly on SPI.com. You can see 10 years of income reports here.
I invested in Gold as per Allens advice and when the big stock market crash occurred in 1987, I made a ton of money by being in other investments such as gold. Ditto for real estate that market plummeted inthe 80's. Following Allen's advice, I was able to pick up loads of real estate at bargain prices becuase most real estate investors back in those days saw real estate only as a tax benefit, not for gains. Their loss.
An obvious example is over exposure to bank stocks, which have been excellent investments for over a century.  Though a foundation of most portfolios, bank stocks do involve more risk at certain stages of the economic cycle than many realise.  Being less exposed to bank shares in the last few months could have preserved some capital.  So, a more diversified approach can help mitigate some of these risks.