I prefer assets that make me a high return for the lowest amount of work possible (semi-passive involvement). And assets that pay me in several unique ways. Cash flow is only one way RE makes money for me. I also get principal reductions, appreciation, tax advantages (depreciation), and I control the rental increases on a yearly basis. Plus a majority of the capital is provided by the secondary market on 30 year fixed low interest rate debt.

If you're looking to get started in real estate, look at a crowd funding solution like RealtyMogul. It works similar to LendingClub - you commit as little as $5,000 towards a property. When the property is fully funded, you become an owner, and will receive your share of the earnings and appreciation in the property.  Check out RealtyMogul to learn more. 
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In 2017, I ended up deploying roughly $611,000 into stocks and $604,327 into municipal bonds. The stock allocation should boost dividend income by about $12,500 a year, and the municipal-bond portion should boost income by about $18,000 a year after tax ($26,000 pre-tax). Therefore, total passive income gets an about $38,500 lift, which recovers over half of my $60,000 loss from selling the house.
In expensive cities like San Francisco and New York City, net rental yields can fall as low as 2%. This is a sign that there is a lot of liquidity buying property for property appreciation, and not so much for income generation. This is a riskier proposition than buying property based on rental income. In inexpensive cities, such as those in the Midwest, net rental yields can easily be in the range of 8% – 12%, although appreciation may be slower.

The second category of passive income is drawing on sources that do not require capital to start, maintain, and grow. These are far better choices for those who want to start out on their own and build a fortune from nothing. They include assets you can create, such as a book, song, patent, trademark, Internet site, recurring commissions, or businesses that earn nearly infinite returns on equity such as a drop-ship e-commerce retailer that has little or no money tied up in operations but still turns a profit.


Or you could do joint ventures/strategic alliances for your business or for other businesses and make residual cash flow for $0 investment.. that’s what I do lol. No money, no risk, little time, 20+ years working from home. Just connect companies and take a %, use the Internet to do it locally or globally, be the intermediary & connect companies…. ;-)
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.
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Loans for service members currently on active duty entail similar residual income standards, but these are typically lower by some 5%. Furthermore, if you have any dependents (children, parents, spouses), who are financially self-reliant and can make proof of their sources of net income they earn (like jobs or other ways of making a living), which could offset their own debt, you can write them off your RI standard list.
Real estate is the obvious choice if you are going to make money on your money. I personally am not at the point where I can do any of this in a meaningful way BUT my parents are and they now own a couple homes outright and are collecting income from them to power their retirement income. It makes a lot more sense for anyone that has a chunk of cash sitting in the bank and are planning on slowly drawing from it because you technically still have all that money in a property (or multiple properties) and can sell them if you really need the lump sum of cash but you’ll earn great interest payments until you do that.
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