We are going to start with 1.5 years of all spending needs in cash. We will draw 1800 to 1900 per month. We will add to this from the index funds by taking a portion of the gains in good years to supplement. This is the total return portion of the equation. Obviously, if stocks decrease drastically over a 5 year period, then I would have to reload by selling some of the ETF holdings.

For someone my age, I have an extremely low risk portfolio of mutual funds, foreign currency, and bonds. It’s made a bit more risky by my recent exposure to cryptocurrency, but that’s the only “high risk” activity going on here. Nothing exciting, but it pays some nice dividends and beats the hell out of keeping money in a savings account. This is a way for me to hedge against the risk I incur by angel investing in startups.
Another way to reduce the work needed when buying rental properties is to buy turn-key properties. Turn-key rentals are already repaired, already rented and already managed by a property manager. Buying a turn-key rental property is as easy as talking to a turn-key rental property about what they have in inventory, picking one and setting up closing. I would still complete due diligence on any turn-key rental property provider to make sure they are a good company. I am considering buying a turn-key property myself and I discuss the process here.

Focus on your primary passive income stream first. It's difficult to grow your passive income into multiple streams if you don't already have one, solid stream. Focus all of your efforts on that one project first and help it grow as productive as possible. Then, you can take the money you've made and lessons you've learned from this passive income stream and put them into others.
Courses are similar to guides but they’re easier to produce for some subjects, especially tech subjects. If you’ve got a computer, a decent microphone and some screen recording software, it’s pretty easy to create high quality courses. You can sell your course through your own site or you can use a marketplace like Udemy to do all the heavy lifting. 
Absolutely Federico. I still invest in real estate but no longer carry the misconceptions that it’s passive income. Fortunately, I’ve held my real estate properties long enough that they cash flow even after paying for management but it was a lot of work in the beginning. Real estate is a great investment but passive income investors should look to REITs and other investments rather than direct investment.
* I use Personal Capital to track all my finances in one place. It’s much easier to use their free software to follow 28 accounts on one platform than to log into various accounts to check my balances. They’ve also got great tools for x-raying your portfolio for excessive fees, recommending a more optimized asset allocation, and planning for retirement with their Retirement Planner.