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Secondly – and this is just quibbling – I’d change that risk score. The risk of private equity is incredibly high and should be considerably riskier than bonds! You are providing a typically very large amount of capital to one business that you agree to have no control over, and the success or failure of that business over a locked, predefined term determines your return. And in the few deals I’ve negotiated for clients, my experience has been that there are often management fees, performance fees, etc. that may cut into your potential gains, anyway. You’re putting a lot of eggs in one basket, and promising an omelet or two to the management no matter what. You really need to be confident that you found the next Uber before you take this giant risk!
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It may also be possible to stagger dispositions of investments between calendar years. For example, if there will already be more than $150,000 of AAII in one year, consider triggering additional capital gains in that year, rather than the next, if that might reduce AAII below the threshold in the next year. Conversely, you may wish to trigger capital gains or losses in a specific year because capital losses cannot be carried forward to a future year for purposes of reducing AAII. As a result, you may wish to realize capital losses and gains in the same taxation year.
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.
P2P lending started in San Francisco with Lending Club in mid-2000. The idea of peer-to-peer lending is to disintermediate banks and help denied borrowers get loans at potentially lower rates compared to the rates of larger financial institutions. What was once a very nascent industry has now grown into a multi-billion dollar business with full regulation.

Passive income is the Holy Grail for online marketers. It's automatic. Effortless. But, not at first. In the beginning, it's grueling. I liken this to doing the most amount of work for the least initial return. However, over time, as your passive income begins to increase, your reliance on an active income plummets. That's when the real magic starts to happen.
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.
Great breakout of some common items that are (mostly) accessible to individuals. My biggest issue with p2p is the ordinary interest it generates and the ordinary tax that we have to pay. That really takes a bite out of the returns. Fortunately, I opened an IRA with one of the providers to juice the return with zero additional risk. 6-8% nominal returns over a long period of time will make me very happy. It should end up as 5-7% of the portfolio anyway, so nothing too significant.
Special rules regarding passive activity losses were enacted in 1986 to limit the amount you could reduce your tax liability from passive income. However, you can still reduce your non-passive income up to $25,000 if your income is below $150,000 and you actively participate in passive rental real estate activities. This amount is phased out between $100,000 and $150,000. Other than this exception, you may only claim losses up the amount of income from the activity. Losses that can not be claimed are carried forward until the property is disposed of or there is adequate income to offset the loss. Real property and other types of investments, if they qualify, may also be used in a 1031 exchange to avoid paying taxes on the income from the sell of the property. This only applies if the proceeds from the sell are used to purchase a similar investment.

If you don’t care about lifestyle design, you can just stay at your current job, right? With financial freedom, you can do whatever you want. You can actually start forming lifestyle design before you are financially free too, just like I have. Even though I spend the majority of my time working on my company, I have positioned myself to be completely on my own schedule, I work whenever I want to for as much or as little time as I want, I sleep in most days, I live at the beach, I can stop working in the middle of the day to go have lunch with a friend, go to the gym, walk the dogs or, shoot, stop working completely for the day and do whatever I want instead! Hiking, snowboarding, surfing, margaritas, whatever.

One of the most appealing options, particularly for millennials, would be #12 on your list (create a Blog/Youtube channel). The videos can be about anything that interests you, from your daily makeup routine (with affiliate links to the products you use), recipes (what you eat each day) or as you mention, instructional videos (again with affiliate links to the products you use). Once you gain a large following and viewership, you can earn via Adsense on YouTube.