Investing your money is one of the oldest passive income strategies on the books. Investing in stocks (or funds of stocks) means that you are becoming a (very) partial owner in the company whose stock you own. When you purchase a stock, your expectation is that the value of the stock will either increase or decrease, and your goal is to buy low and sell high. (This is what everyone is shouting about on the floor of the NYSE in movies about the world of high finance).
They also launched an incredible Retirement Planning Calculator that pulls in real data from your linked accounts to run a Monte Carlo simulation model to output the most likely results of your financial future. I strongly suggest you run your own numbers, play around with the income and expense variables, and see how you stack up. It’s all free and easy to use.
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P.S. I also fail to understand your fascination with real estate. Granted we’ve had some impressive spikes along the way, especially with once in a life time bubble we just went through. But over the long term (see Case Shiller real estate chart for last 100 years ) real estate tends to just track inflation. Why would you sacrifice stock market returns for a vehicle that historically hasn’t shown a real return?
This is the best post I’ve seen on passive income streams. I’m similar to you in that I worked in IBanking for a few years but wanted out. My approach is a little different, instead of starting with the CD’s, I’m trying to build up my net worth with riskier asset classes such as stocks and real estate to get the benefit of compounding. Then, as I approach my retirement year goal, I’ll start moving them into CD and bond ladders. In theory at least, it’s best to have the highest net worth just before retirement, then convert them to risk free passive income. You’re method is more patient and probably more practical than mine. I guess I’m willing to take more risks.
As doctors, we most likely fall into the first category. We may be rich in the sense that our salaries are in the higher economic range, however, because of our expenses (houses, cars, student loan debt, private school tuition, practice overhead, etc.) and sometimes poor decisions, we have a tough time accumulating any real wealth. We’re also handicapped by the fact that we start along this financial journey relatively later in life.
Many bloggers and social media influencers build significant residual income through affiliate partnerships. If a blogger promotes or mentions a product on their site, and readers purchase the product through the link provided, the blogger earns a percentage of the revenue. The same goes for social media influencers. If someone promotes a product on Instagram and their followers purchase it through their link, the Instagrammer would receive a portion of that revenue.

To save time and effort, a person can group two or more of their passive activities into one larger activity, provided they form an "appropriate economic unit." When a taxpayer does this, instead of having to provide material participation in multiple activities, they only have to provide it for the activity as a whole. In addition, if a person includes multiple activities into one group and has to dispose of one of those activities, they’ve only done away with part of a larger activity as opposed to all of a smaller one. 
Successful websites almost always have multiple streams of residual income. Setting up a website that brings income with minimal work is the dream of everyone doing business online, and if you are a website business owner who has the knowledge it takes to build and market a business website, you can also gain multiple streams of residual income that will keep generating income long after the initial investment has been made.
Venture debt ($12,240 a year): The first venture-debt fund has returned almost all my initial capital, so I decided to invest $200,000 in the second fund. I took a risk investing $150,000 in my friend's first fund, so I'm hoping there's less risk in the second fund, given he has four more years of experience on top of his 12-plus years of experience running a venture-debt portfolio for another company.
If you're looking to get started in real estate, look at a crowd funding solution like RealtyMogul. It works similar to LendingClub - you commit as little as $5,000 towards a property. When the property is fully funded, you become an owner, and will receive your share of the earnings and appreciation in the property.  Check out RealtyMogul to learn more. 
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