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.

Real-estate crowdfunding ($9,600 a year): Once I sold my SF rental, it was natural to reinvest some of the proceeds into real-estate crowdfunding to keep sector exposure. I didn't invest a lot in some of my favorite real-estate investment trusts because I felt a rising interest-rate environment would be a stronger headwind for REITs. But if I could be more surgical with my real-estate investments by identifying specific investments in stronger employment-growth markets, I thought I could do better.
According to Uncle Sam, you need to be "materially involved" in an enterprise to earn active income. With passive income, it's just the opposite, as the IRS deems you to be earning passive income if you're not materially involved with a profit-making enterprise. By and large, expect income to be taxable if you are engaged in a passive income enterprise. You will need to report earnings to the IRS. 

What’s also really important to realize here is that when I took the exam I was teaching people to study for, I didn’t get a perfect score. In fact, I didn’t even get close to a perfect score. I passed. But I also knew a lot about this exam—way more than somebody who was just getting started diving into studying for it. And it was because of that, because I was just a few steps ahead of them, that they trusted me to help them with that information. To support this, I provided a lot of great free value to help them along the way. I engaged in conversations and interacted in comments sections and on forums. Most of all, I just really cared about those people, because I struggled big-time with that exam myself.
Like we said above, there’s nothing passive about this, but if you can create another type of asset — a system for selling products — then it is. One example is to write a book, and use Amazon Fulfillment Services to automatically print and ship it every time you sell a copy, depositing the money in your account. Another example is Tim Ferriss, who hired overseas assistants to handle everything at BrainQuicken, from the marketing to the reordering. With drop-shipping (having the manufacturer ship directly to your customer), this has become easier, but you should know that it’s still a good bit of human labor to advertise, handle customer service, etc. But, it’s a good option, and you can experiment with automation and delegation as you go along. If you want to know more about this, read The Four Hour Work Week already!
Freelancing is on the verge of going mainstream. Thirty-six percent of the international workforce now freelances, at least part-time. There are also 40.9 million adults in America who are self-employed. Clearly, freelancing is catching on. But with rapid growth come certain challenges, one being an increased competition for well-paying job and price reduction by those who think they can afford low-bidding at least for now.
Similiar to Adsense, Media.net powers the Yahoo! Bing Network Contextual Ads and is probably the second largest contextual advertising company in the world. I've been running some Media.net ads for a few months and the income was very similiar to adsense. Bear in mind that their approval process is a bit more extensive than Google AdSense. -One has to get a certain number of page views monthly to get an account with them.
Returns on real estate investing vary and you don’t want to get into the business based on an estimated return but on your own calculation of what is possible for your local market and for specific properties. I have seen pretty common averages between 8% and 12% a year for single-family residential rentals with cash flow accounting for between 0% and 6% of the return.
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.
As a general rule, the passive activity loss rules are applied at the individual level. Although Internal Revenue Code Section 469 was enacted to discourage abusive tax shelters, its impact extends far beyond shelters to virtually every business or rental activity whether reported on Schedules C, F, or E, as well as to flow through income and losses from partnerships, S- Corporations, and trusts. Generally, the law does not apply to regular C-Corporations although it does have limited application to closely held corporations.
Sam…just read this article and I want to say that this is the best posting on passive income I have ever read…in a blog, article, or book. Thanks for making a difference and being an inspiration as to how it can all be accomplished. One of the great benefits of the internet is that people are willing to share their stories and experiences with each other online. If we had this when I was working professionally (20-40 years ago), it would have saved me from making some rather poor financial decisions that affected my retirement income. In a way, the internet is making up for the loss of financial security in the loss of The Defined Benefit Plan for retirement. Bravo!
And real estate does more than just track inflation – it throws off income (which is important to some people and useful to most). And while your underlying asset is appreciating, the income also grows as rents increase over time. And if you make smart and well-timed purchases, both rents and asset values can increase at well above the rate of inflation.
That strategy seems waaaayyyy less risky than actively picking stocks of supposedly “reliable” stocks that issue dividends, which could be cut at any time due to shifting industry trends and company performance. Dividend investing feels like an overly complex old-school way of investing that doesn’t have a very strong intellectual basis compared to index investing.
The great part about creating truly passive income is the money comes in every month without you having to sell your investment or worry about running out of money when you retire. The returns are also better for me with rental properties, because my cash flow is producing about a 20 percent cash on cash return and that does not even include equity pay down on my loans or appreciation. The appreciation on my rental properties is a bonus for me, while stock market investors are depending on it.
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