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.
“Where a lot of people mess up is they try to build a business or create a product that serves everybody, and by trying to serve everybody, you serve nobody. You have to specialize and niche down and find a market with a pain point that you, based on your experience, based on your education and based on your passion, can help,” he says. Your earnings will directly reflect how well you serve that particular audience, and the more your message resonates with them, the more opportunities you’ll have to sell to them.
When money is lent to a partnership or S-corporation acting as a pass-through entity (essentially a business that is designed to reduce the effects of double taxation) by that entity’s owner, the interest income on that loan to the portfolio income can qualify as passive income. As the IRS language reads: "Certain self-charged interest income or deductions may be treated as passive activity gross income or passive activity deductions if the loan proceeds are used in a passive activity."
For purposes of item (1), above, an item of deduction arises in the taxable year in which the item would be allowable as a deduction under the taxpayer's method of accounting if taxable income for all taxable years were determined without regard to the passive activity rules and without regard to the basis, excess farm loss, and at-risk limits. See Coordination with other limitations on deductions that apply before the passive activity rules , later.
Passive income is earnings derived from a rental property, limited partnership or other enterprise in which a person is not actively involved. As with active income, passive income is usually taxable. However, it is often treated differently by the Internal Revenue Service (IRS). Portfolio income is considered passive income by some analysts, so dividends and interest would therefore be considered passive.
Information may be abridged and therefore incomplete. This document/information does not constitute, and should not be considered a substitute for, legal or financial advice. Each financial situation is different, the advice provided is intended to be general. Please contact your financial or legal advisors for information specific to your situation.

Of course, a book isn’t the only way to get your thoughts to the world nowadays. You could also start a blog, website or YouTube channel to earn some passive income. Besides the creation of your website, videos and content, blurting out your ideas and advice online seems pretty passive. However, it will take a lot of work on your part and time to gain readers, followers and then paid advertisers. You will need to make your content marketable and appealing. That way you continue to gain followers, advertisers and money.
Dan Caplinger has been a contract writer for the Motley Fool since 2006. As the Fool's Director of Investment Planning, Dan oversees much of the personal-finance and investment-planning content published daily on Fool.com. With a background as an estate-planning attorney and independent financial consultant, Dan's articles are based on more than 20 years of experience from all angles of the financial world. Follow @DanCaplinger
Another thing that belongs firmly at the top of passive income ideas lists is affiliate marketing, where you earn a commission for each product or service that you recommend. My new focus these days is on Amazon affiliate websites. The idea is that you talk about, or review products that you can find on Amazon. People visit your website, click on some of your Amazon affiliate links, buy a product on Amazon and you get a commission for any sales, not only for that specific product but for anything they buy within a 24-hour period.
I love travel photography. I spend a bunch of time on credit card churning and manufactured spending, which allows me to travel the world for virtually free. When I’m on the road, I take my camera with me to generate an additional form of passive income. Not only that I truly enjoy travel photography. It is a great hobby for me. Is hobby income passive or nonpassive income?
The Hardy’s used a partner and tax director at an accounting firm with more than 40 years of experience to prepare and file their tax returns. In 2006 and 2007, the Hardy’s reported their income from MBJ as non-passive based on the CPA's professional judgment. They claimed a total disallowed loss and he determined that the income was non-passive based on MBJ's Schedule K-1 that it distributed to Hardy.
Open up the app store and click on your competing app. Sort by “Most Critical”. See what customers have to say. Here’s an example. The top 2 complaints are about syncing issues and ipad compatibility. Those would be the first items you would consider when creating your version. Don’t fall in the trap of copying another app. Also it’s not about copying anything or anyone. Don’t get this mixed up. It’s rare that anyone invents something that is completely revolutionary. It’s usually taking an existing idea and improving it. Our example is taking a meal planning and grocery shopping and porting it to a convenient app. There is already a version on the web and the developer released it on a different platform. The mobile platform.
Starting a blog is one of the most popular side hustles to earn online income. This is because whether you have 10 people or 10 million reading your content, the amount of your effort to write an article is the same. Websites have low start-up costs and you can literally buy your domain, launch your site and have a few pages created in less than an hour. You won’t start making money right away, but you will be building towards that first $1 of income.
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.

What's crazy is that my book income is more than my SF condo-rental income. Yet I didn't have to come up with $1.2 million of capital (the minimum cost to buy my condo today) to create my book. All I needed to create my book was energy, effort, and creativity. I truly believe that developing your own online product is one of the best ways to make money.


Having an extra house, condo or apartment is potentially quite lucrative, especially if  what the tenant pays covers your mortgage, taxes, insurance, etc. Someone else is basically building your pool of wealth because in 10 or 20 years, you’ll have this $100,000+ asset that is paid off. You can sell it for a large chunk of cash, or keep renting it out and have a nice, steady stream of income. The major problem is that managing this isn’t exactly passive, unless you hire a rental management company who generally take one month’s rent out of the year in exchange for doing this.

“There is no such thing as 100% passive income,” says Flynn. “Even with real estate you still have to manage your properties, or even with the stock market, which is potentially passive income, you still have to manage your portfolio. With online business, there is no such thing as 100% passive income — and this is coming from a guy with a blog called SmartPassiveIncome.com. The definition of passive income is ‘building these businesses of automation,’ but in order to keep them automated and keep that trust going with your audience on top of that, you do have to keep it up every once in a while — so a lot of time upfront and a little time after. But there is alway time involved.”
If you qualified as a real estate professional for 2017, report income or losses from rental real estate activities in which you materially participated as nonpassive income or losses, and complete line 43 of Schedule E (Form 1040). If you also have an unallowed loss from these activities from an earlier year when you didn’t qualify, see Treatment of former passive activities under Passive Activities, earlier.

Developing your own passive income stream is an excellent idea if you believe in financial independence. Not only does it give you freedom of time, but it also reduces your stress, anxiety, and fear of the future. In the book Unshakeable by Tony Robbins, he illustrates how investing a couple of hundred dollars a month is all it takes to become a millionaire. This lifestyle empowers you to do the things you love rather than what pays the bills. See the list below.
After these tenants move out, I'm thinking of just keeping the rental empty with furniture. It sounds stupid to give up $4,200 a month, but I really hate dealing with the homeowner association, move-in/move-out rules, and maintenance issues. Given that the condo doesn't have a mortgage and I have to pay taxes on some of the rental income, I'm not giving up that much. The condo can be a place for my sister, parents, or in-laws to crash when they want to stay in SF for longer than a week or two.
There are a couple of problems with direct investment in real estate though. It’s expensive to buy even a single property, a minimum of tens of thousands of dollars, and there’s no way most investors can build a portfolio of different property types and in different regions to protect from those risks when you have all your money in just one or two investments.
My goal is to generate enough passive income (ultimately; for the next few years, I’m definitely working for it both with a day job and property managing my investments) to do what I want, when I want, how I want, and where I want. We all define that “what, when, how, and where” differently, and to each of us, financial freedom means something different.
This is important to understand this because it is a difference of how you spend your time. No-joke big-time investors make money in their sleep without putting in any effort because they invest in passive income investments. If you are putting in effort, while you might be making bank and doing great at it, you are working. You are making a lot of income because you are rocking out a J-O-B. The no-joke big-time investors, if you’ll notice, also put in a lot of effort but their effort is not on what is currently making them income, it is on finding the next thing that will provide them more income!
If a passive activity interest is transferred because the owner dies, unused passive activity losses are allowed (to a certain extent) as a deduction against the decedent's income in the year of death. The decedent's losses are allowed only to the extent they exceed the amount by which the transferee's basis in the passive activity has been increased under the rules for determining the basis of property acquired from a decedent. For example, if the basis of an interest in a passive activity in the hands of a transferee is increased by $6,000 and unused passive activity losses of $8,000 were allocable to the interest at the date of death, then the decedent's deduction for the tax year would be limited to $2,000 ($8,000 − $6,000).
Leveraging the internet to create, connect, and sell is something every creative person should attempt to do. The only risk is lost time and a wounded ego. You can start a site like mine for as little as $2.95 a month with Bluehost and go from there. They give you a free domain name for a year. Forget all the add-ons. Not a day goes by that I’m not grateful for my site.
In order for you to make the kind of passive income you would like you need to make sure the market segment you want to help has critical mass.  If you have the best widget in the world, but only 14 people need or want it, then you don’t have a viable business.  The great article 1,000 True Fans, by Kevin Kelly, cofounder of Wired Research, talks about if you have 1,000 people who are your customer, each paying you $100 a year, you now have $100,000 a year of passive income.  The point is that you don’t need to serve the entire human population, just enough to have critical mass. 

Let me disabuse you of that notion right now: making money online is not so easy and you actually have to know what you’re doing. 10 years ago when self-publishing was booming and affiliate marketing was in its infancy, you could get rich with some sketchiness. Those days are long gone now. Self-publishing has matured and it’s far, far harder to propel your way up the all-important rankings. Google has come down hard on the spam and if there’s any hint of that on your websites, you’ll get penalized which means no search engine traffic sent your way. This is the death of the Internet marketer.
In determining whether qualified nonrecourse financing is secured only by real property used in the activity of holding real property, disregard property that’s incidental to the activity of holding real property. Also disregard other property if the total gross fair market value of that property is less than 10% of the total gross fair market value of all the property securing the financing.
In the case of an activity with respect to which any deductions or credits are disallowed for a taxable year (the loss activity), the disallowed deductions are allocated among your activities for the next tax year in a manner that reasonably reflects the extent to which each activity continues the loss activity. The disallowed deductions or credits allocated to an activity under the preceding sentence are treated as deductions or credits from the activity for the next tax year. For more information, see Regulations section 1.469-1(f)(4).
Of course, a book isn’t the only way to get your thoughts to the world nowadays. You could also start a blog, website or YouTube channel to earn some passive income. Besides the creation of your website, videos and content, blurting out your ideas and advice online seems pretty passive. However, it will take a lot of work on your part and time to gain readers, followers and then paid advertisers. You will need to make your content marketable and appealing. That way you continue to gain followers, advertisers and money.
Active Income Investments: Flipping and wholesaling. You have to do work in order to see money from these. You have to be hands-on. Note: I do still stand by my argument that wholesaling is not actually an investment at all, but for the sake of so many people thinking it is, I am including it. Another note: It is possible, if you are really slick and good, that you could be decently hands-off for a flip. But that is long down the road of being an advanced flipper so for now, I’m leaving it here.
Income tax is a cost of doing business and that cost carries over into the business of real estate ownership and operations. In July 2017, in the depths of the summer, the Federal Department of Finance (“Finance”) announced drastic changes that would have changed that cost of doing business for those owning shares of a Canadian controlled private corporation (“CCPC”). When ultimately distributed to the individual shareholder in the form of a dividend, investment income earned on the retained earnings generated from an active business would have cost the shareholder an ultimate income tax rate equal to 73% of the investment income. These proposed changes to the “passive income” rules were very complex and would have had the potential to shift the after-tax return for CCPCs while leaving the tax burden of public corporations, foreign corporations and tax-exempt entities unaffected.
If you have any questions or you can’t decide how best to invest your assets, consider talking to a financial advisor. A matching tool like SmartAsset’s SmartAdvisor can help you find a person to work with to meet your needs. First you’ll answer a series of questions about your situation and goals. Then the program will narrow down your options from thousands of advisors to up to three registered investment advisors who suit your needs. You can then read their profiles to learn more about them, interview them on the phone or in person and choose who to work with in the future. This allows you to find a good fit while the program does much of the hard work for you.
Depending on the level of AAII otherwise earned in a particular year, you may wish to consider investments that lean towards growth rather than annual interest or dividend income, as you may better be able to time the recognition of a capital gain. In addition, since capital gains are only 50 per cent taxable, it would take $100,000 of realized capital gains to generate $50,000 of passive income that is counted towards the AAII test.

Because passive investors’ rentals are viewed as secondary income, they can only deduct the normal costs associated with their rental properties. They cannot deduct any home office expenses and are limited on how much they can deduct from any losses they might incur. As of 2010, you can only deduct up to $3,000 from your other active income like your job or employment.
If an investor puts $500,000 into a candy store with the agreement that the owners would pay the investor a percentage of earnings, that would be considered passive income as long as the investor does not participate in the operation of the business in any meaningful way other than placing the investment. The IRS states, however, that if the investor did help manage the company with the owners, the investor's income could be seen as active since the investor provided "material participation." 
Peer-to-Peer Lending: Earn up to 10% in returns by lending individuals, organizations and small companies who don't qualify for traditional financing through peer-to-peer lending platforms like Lending Club. You can lend $100, $1,000, or more to borrowers who meet lending platform financial standards. Like a bank, you'll earn interest on the loan - often at higher returns than banks usually get.
Also, financial freedom is different for every person – that’s where lifestyle design comes in. If you determine that you need $4,000 or $8,000/month (your financial limit, as you called it) to allow you to never have to work again and live the kind of life you want, then you have achieved financial freedom through lifestyle design when your passive investments produce that income. It’s a very straight forward concept, and tons of investors have proved it’s doable.
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.
That is a nice list of passive income sources. Actually, the most up-to-date list of dividend growth stocks is the list of dividend champions, maintained by Dave Fish. The list of dividend aristocrats is incomplete at best. For example, the dividend champions list has over 100 companies that have managed to increase dividends each year for at least 25 years in a row. The list of dividend aristocrats has no more than 50 – 60.

Generally, any gain or loss on the disposition of a partnership interest must be allocated to each trade or business, rental, or investment activity in which the partnership owns an interest. If you dispose of your entire interest in a partnership, the passive activity losses from the partnership that haven’t been allowed generally are allowed in full. They also will be allowed if the partnership (other than a PTP) disposes of all the property used in that passive activity.
A working interest in an oil or gas well which you hold directly or through an entity that doesn’t limit your liability (such as a general partner interest in a partnership). It doesn’t matter whether you materially participated in the activity for the tax year. However, if your liability was limited for part of the year (for example, you converted your general partner interest to a limited partner interest during the year) and you had a net loss from the well for the year, some of your income and deductions from the working interest may be treated as passive activity gross income and passive activity deductions. See Temporary Regulations section 1.469-1T(e)(4)(ii).
Qualified dividends are taxed the same as long-term capital gains. In 2018, you can earn up to $38,600 in ordinary income without being taxed on long-term capital gains or qualified dividends. If you earn between $38,600 and $425,800 in ordinary income, your long-term capital gains tax rate is 15 percent, which would also apply to qualified dividends. If you make more than $425,800, the rate is 20 percent.
Passive income differs from active income which is defined as any earned income including all the taxable income and wages the earner get from working. Linear active income refers to one constantly needed to stay active to maintain the stream of income, and once an individual chooses to stop working the income will also stop, examples of active income include wages, self-employment income, martial participation in s corp, partnership.[4] portfolio income is derived from investments and includes capital gains, interest, dividends, and royalties.[5]

One aspect you might want to add to your scoring is “inflation protection”. At one end, bonds and CDs generally pay a fixed nominal coupon that doesn’t rise with inflation. Stock dividends and Real estate rents (and underlying property value) tend to. Not reallly sure how P2P lending ranks- though I suppose the timeframes are fairly short (1 year or less?) and therefore the interest you receive takes into account the current risk free rate + a premium for your risk. Now that I think about it, P2P lending probably deserves a lower score in the activity column than bonds too (since you probably need to make new loans more often).
What about getting hit with AMT (Alternative Minimum Tax) in cases your passive income / capital gains are too high? I’m not that familiar with the details of AMT, but I got hit with AMT one time due to an “exercise and hold” of ISOs (stock options). My CPA explained it’s another method of calculating my tax liability, and in cases I gain too much capital gains, the IRS may treat and tax them as ordinary income.
Dan Caplinger has been a contract writer for the Motley Fool since 2006. As the Fool's Director of Investment Planning, Dan oversees much of the personal-finance and investment-planning content published daily on Fool.com. With a background as an estate-planning attorney and independent financial consultant, Dan's articles are based on more than 20 years of experience from all angles of the financial world. Follow @DanCaplinger

Passive income differs from active and portfolio income. However, despite its name, passive income doesn’t always mean you can sit back idly while you earn money. In fact, the IRS also includes in its definition of passive income as “net rental income” and sometimes self-charged interest. This means to begin earning passive income, you’ll need to invest some time and/or money at least at the start. Because the IRS still views it as income, that means passive income is subject to taxation.
If you’re looking for an investment that offers a seamless user experience, real estate crowdfunding is your tool. Companies like RealtyMogul.com connect investors to debt and equity investment opportunities online, without the hassle of dealing with large banks or financial institutions. The online functionality appeals to all skill levels, from first-timers to veteran investors. In just a few clicks, investors can access the best real estate deals.
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