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.
A planning opportunity may be available by converting a primary residence into rental real estate.  For example, Mary purchases a condo in 2010 and in 2013 decides to upgrade into a single family home.  She rents out the condo to earn some money.  Due to recent developments in the area, the condo is now worth much more and she sells it for a gain of $100,000.  Since Mary lived in the home for 2 out of the past 5 years, the entire gain is excluded from income.  The 2 year rule can occur anytime during the 5 year period and does not have to be consecutive.  Keep in mind though that if you do the opposite and convert rental property to a primary residence, the rules are more complex and the gain exclusion tends to be limited.
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.
​Udemy is an online platform that lets its user take video courses on a wide array of subjects. Instead of being a consumer on Udemy you can instead be a producer, create your own video course, and allow users to purchase it. This is a fantastic option if you are highly knowledgeable in a specific subject matter. This can also be a great way to turn traditional tutoring into a passive income stream!
Pursuing passive income can be the right move for you, especially if you just need some extra cash to pay off debts. It’s important, though, that you find the right side hustle for you and your lifestyle. There’s no point in creating passive income if it’s not passive at all. Decide how much time and money you have to spare. Then choose the passive income venture that will prove most worthwhile.
In 2017, I ended up deploying roughly $611,000 into stocks and $604,327 into municipal bonds. The stock allocation should boost dividend income by about $12,500 a year, and the municipal-bond portion should boost income by about $18,000 a year after tax ($26,000 pre-tax). Therefore, total passive income gets an about $38,500 lift, which recovers over half of my $60,000 loss from selling the house.
In terms of the returns, peer-to-peer lending can be profitable, particularly for investors who are willing to take on more risk. Loans pay a certain amount of interest to investors, with the highest rates associated with borrowers who are deemed the biggest credit risk. Returns typically range from 5% to 12%, and there's very little the investor has to do beyond funding the loan.
MBJ is an LLC formed by a group of practicing physicians in 2004 for the purpose of operating a surgery center. For income tax purposes, it is treated as an LLC, and it hires its own employees. It bills patients directly for facility fees and then distributes each members' share to him or her based on his or her share of the earnings, which is the facility fees less expenses. It uses a third-party accounting firm to prepare the Schedule K-1, Partner's Share of Current Year Income, Deductions, Credits, and Other Items, and all other accounting matters for the members. MBJ does not pay members/managers for the procedures they perform.
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.
In expensive cities like San Francisco and New York City, net rental yields can fall as low as 2%. This is a sign that there is a lot of liquidity buying property for property appreciation, and not so much for income generation. This is a riskier proposition than buying property based on rental income. In inexpensive cities, such as those in the Midwest, net rental yields can easily be in the range of 8% – 12%, although appreciation may be slower.
A former passive activity is an activity that was a passive activity in any earlier tax year, but isn’t a passive activity in the current tax year. You can deduct a prior year's unallowed loss from the activity up to the amount of your current year net income from the activity. Treat any remaining prior year unallowed loss like you treat any other passive loss.
Additionally, if you wrote a book and receive royalty checks, that income is also passive and not subjected to self-employment taxes. But, if you write several books or make updates to an existing book (like this one) then you are materially participating in your activity and your income is earned income. And Yes, you would pay self-employment taxes on that income.
If you’re looking for a way to begin gradually replacing your income, these are just some of the best ways you can do it as a physician. Remember the idea of gradual retirement? Passive income streams like the ones mentioned here are perfect ways to allow you to spend more time with family, enjoy your day job more, and, of course, make a little money while you’re at it.
In 2012, even I wrote a 150-page eBook about severance package negotiations that still regularly sells about ~35 copies a month at $85 each (2nd edition for 2017) without any effort. In order to generate $2,975 a month or $35,700 a year in passive income as I do now, I would need to invest $892,500 in something that generates a 4% yield! To earn $10,000 a year in passive income would therefore need roughly $250,000 in capital.

With the objective of circumventing this 4% tax deferral, the 2018 federal budget proposes, with certain exceptions, to limit the access to the RDTOH pool in circumstances where the dividend paid by the corporation is a dividend that is an Eligible Dividend. The idea here is to align the refundable tax paid on passive income with the payment of dividends sourced from that passive income. The new measures apply for taxation years starting after 2018 and will require the tracking of two RDTOH pools for CCPCs.


MBJ is an LLC formed by a group of practicing physicians in 2004 for the purpose of operating a surgery center. For income tax purposes, it is treated as an LLC, and it hires its own employees. It bills patients directly for facility fees and then distributes each members' share to him or her based on his or her share of the earnings, which is the facility fees less expenses. It uses a third-party accounting firm to prepare the Schedule K-1, Partner's Share of Current Year Income, Deductions, Credits, and Other Items, and all other accounting matters for the members. MBJ does not pay members/managers for the procedures they perform.

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The amount you have at risk in any activity is reduced by any losses allowed in previous years under the at-risk rules. It may also be reduced because of distributions you received from the activity, debts changed from recourse to nonrecourse, or the initiation of a stop loss or similar agreement. If the amount at risk is reduced below zero, your previously allowed losses are subject to recapture, as explained next.
Obviously, these are much higher than you’re going to get with most other investments. What’s more is that you can choose a plan that matches your investment strategy, whether your goal is Supplemental Income, Balanced Investing, or Long-term Growth. You can also look at different real estate projects and choose for yourself which ones to invest in.
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