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”.
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.

I’m a 45 year old business owner who also has focussed on diversifying my income streams. I have a short term vacation rental in Florida that I bought for $390k in 2012 and net rental income for the last three years has been growing steadily. 2015 I am at $70k gross right now but should end up at $80-85k with net around $45k plus we use the place about 35 nights a year.
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”.
When you invest in a dividend-paying stock, you are buying a share of the company and you literally become part-owner of that business. As the company grows and generates extra cash that it doesn’t necessarily want to re-invest, it might decide to return some of the extra cash to the shareholders in the form of dividends. And because you own a fraction of the company, you will receive a portion of the cash!
The Volunteer Income Tax Assistance (VITA) program offers free tax help to people who generally make $54,000 or less, persons with disabilities, and limited-English-speaking taxpayers who need help preparing their own tax returns. The Tax Counseling for the Elderly (TCE) program offers free tax help for all taxpayers, particularly those who are 60 years of age and older. TCE volunteers specialize in answering questions about pensions and retirement-related issues unique to seniors.
In fact, as I laid in bed one morning coming up with this post, I could really only think of one aspect of passive income that is worse than earned income. If you are a high earner, you can’t deduct real estate losses against your earned income unless you qualify as a “real estate professional,” which basically means you spend > 750 hours a year doing it. That’s it. The rest of the time, passive beats active.

Those who don't meet this test can qualify for a limited $25,000 allowance for losses if they qualify as an active participant. Active participation requires only limited activities, such as approving new tenants, setting rental terms, and approving payouts. If you qualify, you can then take up to that limited amount of loss each year, carrying over any excess losses until you generate rental income to offset it.
When withdrawing money to live on, I don’t care how many stock shares I own or what the dividends are – I care about how much MONEY I’m able to safely withdraw from my total portfolio without running out before I die. A lot of academics have analyzed total market returns based on indices and done Monte Carlo simulations of portfolios with various asset allocations, and have come up with percentages that you can have reasonable statistical confidence of being safe.
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.
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.
​Self Publishing is mainstream today. When you purchase an eBook off of Amazon there’s a pretty good chance you’re buying a self-published book. Self-publishing is also ridiculously easy. I tried this a few years ago and couldn’t believe how simple the process was. To self-publish a book you’ll first need to write and edit it, create a cover, and then upload to a program such as Amazon’s Kindle Direct Publishing. Don’t expect instant success though. There will need to be a lot of upfront marketing before you can turn this into a passive income stream.
Oh it matters. It matters because accomplishing your goals depends on understanding these terms very clearly. What is the most common reason investors give as to why they are getting into real estate investing or why they are already in it? Financial freedom. Those who want financial freedom very clearly define that goal as being able to use real estate as a vehicle to eventually break loose of their current career and not have to work for their income. Okay, cool, a goal! And an amazing goal at that. Okay, so financial freedom, let’s talk about that.
However, self-publishing is a good option for generating passive income and fits very well with the “work-up-front, reap benefits later” model. It’s a ton of work to write a book, especially when you’re just getting everything like editing, formatting, cover design, and book descriptions all figured out. But, once you do all that work, you can upload it to Amazon and then hopefully keep earning commissions for months or even years.

Crowdfunding is a newer way to invest, having emerged onto the scene just within the last few years. Most people have heard of sites like Kickstarter and GoFundMe, and a very similar concept exists for real estate. Developers are always looking to raise capital to fund their projects. Through the various online platforms, investors have access to these projects and can choose to invest in both residential and commercial properties. See the List of My Favorite Crowdfunding Sites.
One side note worth highlighting here – it is a common misconception that passive investment income earned within a corporation can be taxed at the lower small business tax rate. This is incorrect as passive income is generally taxed at about the same rate (over 50%), whether earned inside or outside a corporation, so there is no real benefit, per se, from earning investment income in a corporation. Rather, the advantage is that the corporate entrepreneur is able to temporarily invest the amount of taxes deferred by delaying the withdrawal of funds from his/her company.

Thanks for writing this Mr. Samurai. I just got over the student loan hump but I feel pretty good about it at 27 having a graduate degree and being 100% debt free. Now that I’m on the other side it is good for my brain to absorb some of your knowledge regarding passive income investments. I love gleaning wisdom from older folks who have been there and done that. Mentors rock!

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.
The IRS defines depreciation losses as “allowances for exhaustion, wear and tear (including obsolescence) of property.” According to their website, “You begin to depreciate your rental property when you place it in service. You can recover some or all of your original acquisition cost and the cost of improvements by using Form 4562, Depreciation and Amortization, (to report depreciation) beginning in the year your rental property is first placed in service, and beginning in any year you make improvements or add furnishings.”
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If you can max out your 401k or max out your IRA and then save an additional 20%+ of your after-tax, after-retirement contribution, good things really start to happen. If one is looking for earlier financial independence, such as retiring in their 40s or early 50s, it may be a good idea to skew towards more after-tax savings and investments given one has to wait until 59.5 to withdraw from their 401k or IRA penalty-free.


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.
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