6) Always Remember That Everything Is Relative. The best way to determine worthwhile passive income streams is by comparing the likely return (IRR) with the current risk-free rate of return. If I round up, the 10 year bond yield is at 3%. Any new venture should thoroughly beat 3% otherwise you are wasting your efforts since you can earn 3% doing nothing.
Lending Club went public in 2014 and is now worth about $1.7B. They advertise P2P lending returns of over 7% for well-diversified portfolios of over 100 notes. I’ve personally been able to achieve a 7.4% annual return over the past two years in a completely passive way by investing in A and AA notes. Others have achieved a 10% annual return through relatively minimum effort.
In my situation, I knew that I would be leaving San Diego and quitting my job many months in advance. I knew when we’d be leaving but I didn’t know where we’d be heading(since my fiancee was applying to med school). That really forced me to think outside of the box and come up with some unique ways to make money, independent of our future location. I could have sat back and hoped that she got into a school in a city where I could find work as an engineer but I didn’t want to rely on chance.
It’s a (mostly) short term, higher risk, higher reward place to invest cash that has a low correlation with the stock market, but is far more passive than buying and managing properties, has more opportunity for diversification than private placements (minimums of 5-10K, rather than 100K), and most of the equity offerings (and all of the debt offerings) provide monthly or quarterly incomes. Unlike a REIT, you can choose exactly which projects you wish to invest in.

If you need cash flow, and the dividend doesn’t meet your needs, sell a little appreciated stock. (or keep a CD ladder rolling and leave your stock alone). At the risk of repeating myself, whether you take cash out of your portfolio in the form of “rent”, dividend, interest, cap gain, laddered CD…., etc. The arithmetic doesn’t change. You are still taking cash out of your portfolio. I’m just pointing out that we shouldn’t let the tail wag the dog. IOW, the primary goal is to grow the long term value of your portfolio, after tax. Period. All other goals are secondary.
Portfolio income can come from multiple sources – interest/bond coupons, stock dividends, financial strategies including derivatives and capital growth.  Each offers some cash flow and some also offer potential capital gain with some risk from liquidity and volatile prices.  In this low-yield environment, many investors rely too heavily on cash flows and to pursue this are venturing further into riskier areas than they’d normally consider.
Anthony, nice setup! To your question about the rental mortgages, you haven’t said what interest rate you are paying. As a start, if you are paying more than the risk free rate (Treasury bills) which you probably are, then a true apples to apples comparison would be yes, pay off the mortgage. But, if you are comfortable taking more risk, you have other options to invest in which you *hope* will yield you more over the coming years. You also didn’t say whether the rentals generate net income and if so, how much? What is the implied rate of return on the equity you have invested in them? If you pay the mortgages off, you’ll have even more equity tied up, will the extra net income make that worthwhile? Maybe you should use the money to buy more rentals instead, if purchase opportunities still exist in your town. … this is less of an answer than a framework to analyze the decision, hope it is helpful.

Andrew Rafal, Founder and President of Bayntree Wealth Advisors in Arizona, recently told me about his push to get clients to diversify their income streams. The Great Recession feels like an eternity ago now that the economy is looking up, he says. The job market is strong and consumer confidence is through the roof. As a result, it’s possible people are getting a little too comfortable.