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.
What I find most interesting is the fact that I had never considered options like LendingTree or realityshares for other income sources. Investing in property has been too much of bad luck for people that I know personally, so I am interesting in getting involved in a situation where I would have to be dealing with maintenance issues or tenants. There are services for you to do that, but I had not come across any that didn’t eat most if not all of the earnings. Then again, I live in the NY area. Investing in the midwest would not be reasonably possible for me, directly, but reading about realityshares is something I am going to look into further. That might be a real possibility.
Whether you take a “distribution” (aka free-cash-flow) in the form of a dividend, interest payment, capital gain, maturing ladder of a CD, etc, you are still taking the same amount of cash out of your portfolio. Don’t fall for the trap of sub optimizing your overall portfolio’s performance because your chasing some unimportant trait called “income”.
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.
REITs provide an easy way to get real estate exposure in your portfolio but it is crucial that you avoid asset class overlap.  Since many stock and index funds include REIT companies, having a separate allocation to REITs in a portfolio may create double counting.  Certain fund managers strip out REIT companies from their equity investments to avoid this issue.  One example is Dimensional Fund Advisors.  For those who want real estate exposure without the hassle of being a landlord, purchasing REITs may be the way to go.
Book sales ($36,000 a year): Sales of How to Engineer Your Layoff" continue to be steady. I expect book sales to rise once the economy starts to soften and people get more nervous about their jobs. It's always best to be ahead of the curve when it comes to a layoff by negotiating first. Further, if you are planning to quit your job, then there is no downside in trying to engineer your layoff so you can get WARN Act pay for several months, a severance check, deferred compensation, and healthcare.
ie first you need to haul ass and do something crazy, eg write a quality 20,000 word ebook (insanely not passive hahahah), but then you get to sit back and enjoy seeing PayPal sale messages pop up on your iPhone each morning as sale after sale after sale is made…on an ongoing basis and without any additional work. That’s some seriously Pina Colada flavored passive goodness!
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.
You can’t start charging right off the bat without your audience knowing anything about the value you offer (though you could still indirectly earn money from them with the right ads). “The best way to go in terms of a long-term passive income business [is] delivering value and information for free, and therefore establishing expertise, knowledge and trust with your audience,” says Flynn.

If you’ve ever thought to yourself, “I wish there was a product that did this,” then invent it! Create a product, medical or otherwise, and sell it as a company or get royalties for it. It’s not impossible to figure out, I have many friends who have taken a concept to market. Don’t overlook an invention as a fantastic means of attaining passive income.
“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.

Fulfillment by Amazon (FBA) is another model that has been gaining popularity in recent months. The major difference from the model that I described above is that instead of shipping it to a warehouse, you ship it directly to Amazon. For a cut of the money on each sale (and they also charge storage costs), they package it all up and send out your order. You make less money than doing it yourself, however once set up, it does have the hands-off factor going for it.
If the amount you had at risk in an activity at the end of your tax year that began in 1978 was less than zero, you apply the preceding rule for the recapture of losses by substituting that negative amount for zero. For example, if your at-risk amount for that tax year was minus $50, you will recapture losses only when your at-risk amount goes below minus $50.

You can’t start charging right off the bat without your audience knowing anything about the value you offer (though you could still indirectly earn money from them with the right ads). “The best way to go in terms of a long-term passive income business [is] delivering value and information for free, and therefore establishing expertise, knowledge and trust with your audience,” says Flynn.
Similar to making a website or blog, but more passive, is creating an online course. If you have a specific skill you know you can teach and that others want to learn, you can easily create an online course. Sites like Udemy can help you do this. It requires some work to make it, but after that, users simply need to sign up for the course and pay a fee.
Role of “real estate professional” can be well played by a non-working or stay-at-home spouse. If you’ve got one who’s willing of course. 🙂 Under current tax law, with a spouse/real estate professional materially participating in the rental property activities, the 3.8% Medicare tax (discussed in Section 1) can be entirely avoided. So, while there is a bit of burden in meeting the requirements, this could be a great play for a Doc and a real estate professional spouse who want to take unlimited real estate losses against regular earned income AND shelter any gains from the additional 3.8% tax.
This publication discusses two sets of rules that may limit the amount of your deductible loss from a trade, business, rental, or other income-producing activity. The first part of the publication discusses the passive activity rules. The second part discusses the at-risk rules. However, when you figure your allowable losses from any activity, you must apply the at-risk rules before the passive activity rules.
In 2006, Dr. Hardy purchased a 12.5% interest membership in MBJ for $163,974. During the year following this purchase, the Hardy’s decided to build an office for Northwest Plastic Surgery next to MBJ. Dr. Hardy had no day-to-day responsibilities at MBJ, never managed it, and did not have any input about management decisions. He primarily performed surgeries on MBJ's patients on Mondays, and he did not pay rent to perform surgeries at MBJ. He received a distribution from MBJ regardless of whether he performed any surgeries at MBJ, and this distribution was not dependent on how many surgeries he performed. Physicians cannot refer their patients to the surgery center when they hold a financial interest. However, the patients often choose the surgery center because it was cheaper.
In June, he put ads on his site with Google Adsense, and within the first hour, earned $1.08 with three clicks. He earned $5 the first day, $7 the second, and then eventually began pulling in $15-$30 a day. In October, he created an ebook exam study guide priced at $19.99. By month’s end, he earned $7,906.55 — more than he had ever previously earned in a month.

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.
An item of deduction from a passive activity that’s disallowed for a tax year under the basis or at-risk limitations isn’t a passive activity deduction for the tax year. The following sections provide rules for figuring the extent to which items of deduction from a passive activity are disallowed for a tax year under the basis or at-risk limitations.

Logan is a CPA with a Masters Degree in Taxation from the University of Southern California. He has been featured in publications such as Debt.com. He has nearly 10 years of public accounting experience, including 5 with professional services firm Ernst & Young where he consulted with multinational companies and high net worth individuals on their tax situations. He launched Money Done Right in 2017 to communicate modern ideas on earning, saving, and investing money.
The E-Commerce model is an interesting one. The idea is that you get products made cheaply (usually China) through a site like Alibaba, ship them to a warehouse (or your own house!), put the product description up on Amazon (or your own website), get some sales and then send out the product. There is a big learning curve with this one and you need some money up-front to get the products.
Real estate investments generally are considered passive income – unlike income from a job, which is considered active – because revenue is generated from the money you invested rather than from the work that you do. You have to pay taxes on your income regardless of whether it's active or passive. Money earned from real estate investing is reported on the Schedule E form and gets carried forward to line 17 of your 1040 tax return. It's then included with your other income and is subject to regular taxes.
I own several rental properties in the mid west and I live in CA. I have never even seen them in person. With good property management in place (not easy to find but possible) it is definitely possible to own cash flowing properties across the country. Not for everyone and not without it’s drawbacks, but it seems to be working for me so far. I’m happy to answer any questions about my experience with this type of investing.
In a worst-case scenario, a complete loss of the SBD, which would only occur when the AAII is greater than $150,000, means that $500,000 of income that would have been taxed at the low rate of, say 12.5 per cent in Ontario in 2019, would be taxed at the higher, general rate of 26.5 per cent. That difference, representing 14 per cent, translates to $70,000 less to invest, which can make a big difference with years of investing.
I also noticed that in your passive income chart at the bottom that you don’t include your internet income other than sales from your book. Is there a reason for that? Do you not consider is passive because you are actively blogging all the time to create it? Or do you just not want readers to know how much money you generate from blogging activities?
If any amount of your pro rata share of an S corporation's loss for the tax year is disallowed under the basis limitation, a ratable portion of your pro rata share of each item of deduction or loss of the S corporation is disallowed for the tax year. For this purpose, the ratable portion of an item of deduction or loss is the amount of such item multiplied by the fraction obtained by dividing:

Herbert and Wilma are married and file a joint return. Healthy Food, an S corporation, is a grocery store business. Herbert is Healthy Food's only shareholder. Plum Tower, an S corporation, owns and rents out the building. Wilma is Plum Tower's only shareholder. Plum Tower rents part of its building to Healthy Food. Plum Tower's grocery store rental business and Healthy Food's grocery business aren’t insubstantial in relation to each other.

It was easier recouping the lost $60,000 in rental-property income than I expected. For so long, my primary mindset for passive income was rental income. Having $815,000 less mortgage debt but still generating roughly the same amount of passive income with a much larger cash balance feels great. Further, my passive-income portfolio got even more passive, which is good as a stay-at-home dad to a newborn.
Add Leverage (Mortgage) and you greatly increase the ROI especially from the perspective of using Rents (other peoples money) to pay down the mortgage and increase your equity in the property over time. At this point then yes price appreciation is secondary bonus and we have an arguement of how and why Real Estate can be better than Growth Stocks in some scenarios and for some investors.
You don’t have to be a big corporate executive to need an assistant. Filing, emailing, scheduling and organizing the results of your moneymaking ventures takes time. And that's time you don’t want to waste while building your passive income empire. Nor do you want to expend any more time and money training and paying a new employee than you need to. Instead, consider hiring a virtual assistant.
If you make the choice, it is binding for the tax year you make it and for any later year that you are a real estate professional. This is true even if you aren’t a real estate professional in any intervening year. (For that year, the exception for real estate professionals won’t apply in determining whether your activity is subject to the passive activity rules.)
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The at-risk rules limit your losses from most activities to your amount at risk in the activity. You treat any loss that’s disallowed because of the at-risk limits as a deduction from the same activity in the next tax year. If your losses from an at-risk activity are allowed, they’re subject to recapture in later years if your amount at risk is reduced below zero.


You could also do this by charging for financial plans and managing people’s investments.  The fee’s you charged would be recurring as long as you managed the relationship to keep them happy.  This approach to passive income has a much higher barrier to entry due to needing qualifications, licenses, and building relationships over time.  If done correctly, it can be a very lucrative source of passive income.
The activity is a personal service activity in which you materially participated for any 3 (whether or not consecutive) preceding tax years. An activity is a personal service activity if it involves the performance of personal services in the fields of health (including veterinary services), law, engineering, architecture, accounting, actuarial science, performing arts, consulting, or any other trade or business in which capital isn’t a material income-producing factor.
It is helpful to have an understanding of the bigger tax items – basis and depreciation.  Basis is the cost or purchase price of the property minus the value of the land (note: you cannot depreciate land).  The depreciation deduction you can take on residential real estate per year is the basis (cost less land) divided by 27.5.  Depreciation is a great tax deduction you can take every year but will affect your gain or loss when you sell the property.
Since David may never be coming back to this site, If anyone other than David can point me in the right direction, Id greatly appreciate it. I live in Chicago, and I need to buy a quality rental to hold long term somewhere but I have no idea where, and I really don’t want to buy in Chicago. Chicago is insanely corrupt and in HUGE debt. I cant leave Chicago in the near term, I take care of an aging parent, and if I left, my salary would drop by 50%. Id still like to diversify into a rental property.. but I feel that if I just call up a stranger, they’d attempt to sell me their best pig with lipstick, and pressure me to jump on the deal before someone else ‘stole’ it. I have no problem hiring a property inspector from a different city, but don’t want to waste hundreds of dollars if the agent is steering us towards crap property after crap property. I’m looking for broad advice. Any constructive reply appreciated. Thanks guys.
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.

Role of “real estate professional” can be well played by a non-working or stay-at-home spouse. If you’ve got one who’s willing of course. 🙂 Under current tax law, with a spouse/real estate professional materially participating in the rental property activities, the 3.8% Medicare tax (discussed in Section 1) can be entirely avoided. So, while there is a bit of burden in meeting the requirements, this could be a great play for a Doc and a real estate professional spouse who want to take unlimited real estate losses against regular earned income AND shelter any gains from the additional 3.8% tax.
Now, under the regime proposed by the 2018 federal budget, the same corporation would not be eligible for a refund of its RDTOH upon the payment of the Eligible Dividend. Instead, the corporation will obtain its RDTOH back only if the dividend paid is a dividend other than an Eligible Dividend. This will therefore eliminate the deferral of the additional 4% income tax.
Generally, rental activities are passive activities even if you materially participated in them. However, if you qualified as a real estate professional, rental real estate activities in which you materially participated aren’t passive activities. For this purpose, each interest you have in a rental real estate activity is a separate activity, unless you choose to treat all interests in rental real estate activities as one activity. See the Instructions for Schedule E (Form 1040), Supplemental Income and Loss, for information about making this choice.
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…. ;-)
What is passive income?  It is income that is not generated from your day job.  Any net gain at the end of the year is taxed at ordinary income tax rates.  The additional downside: if the rental property generates a loss, you are not able to offset passive losses with ordinary income i.e., wages.  The passive losses can only be used to offset passive income.
The IRS requires REITs to pay out at least 90% of its income to shareholders.  Thus, REITs tend to be higher yield since a large fraction of the earnings come out as dividends, which may be beneficial for certain income oriented investors.  The flipside is the tax cost for investing in REITs since income must be distributed and as a holder the taxes flow through to you.
I have only dabbled in drop-shipping before when I had an eCommerce platform 6 years ago or so. I think it is something that you could do on the side, but you would want to do in depth research on the industry you want to get into before setting up shop. It may be a little less passive up front, but over time you could take your hands off the wheel.
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