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.
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.

Once your audience has grown and you have validation that you’re offering them value, there are many ways to create passive income. You could sell digital products like ebooks or courses, take up affiliate marketing in which you promote other company’s products and earn a commission when you sell that item to your audience, build a community and charge people to be a part of it, create software and sell that, among other avenues. Ask your audience directly what would serve them best, or look at what they’re saying on Twitter, Facebook or other websites, to find out what problems they have and how you could help solve them.
I am still working on my passive income, however I like multiple income streams even more. My favorite is capital gains because it is one of the lowest rates. One of the best passive income streams is a pension/Social Security. As I near retirement, I like the concept of it supporting my needs and my 401k supporting my wants. In addition, my brokerage accounts are all at capital gains rates. Don’t misunderstand, I am still working on adding more because I like multiple income streams!

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.
Seeing the residential real estate boom coming, I started buying single-family rentals in 2002. I learned a lot about real estate investing and passive income properties over the next five years. As someone that has flipped houses as well as managed a group of rental properties, the best advice I can offer is to know yourself and how much time you are willing to spend on the business. 

Earn royalties from writing books, songs or developing products. You can even buy someone else's share of a song via a writer's auction. For example, if a songwriter dies, his/her heirs have the right to auction off a percentage of their songs during an estate sale. You bid on a song, and if it's accepted, you own a piece of it and receive a royalty check each month, which can be deposited into your savings or checking account or a special savings account like a financial freedom account.
Like many, I was first really turned on to the idea of passive income by Tim Ferriss. In The Four Hour Work Week, he describes the system he developed with BrainQuicken, where the marketing, shipping, reordering, banking, and even customer service of the company was on complete auto-pilot. I found this idea intoxicating. The idea that Tim could travel the world learning to tango and staying on private islands while money just accumulated in his bank account seemed like some strange fiction — surely, this isn’t how people actually live, is it?
This is an ideal strategy if you live in an area where real estate prices are too high to realistically invest in, or you don’t want the hassle and expense of traveling all over the country visiting potential properties. Plus, if you are new to single-family real estate investing, letting a place like Roofstock guide you through the process is a great way to get your feet wet. https://www.mamafishsaves.com/wp-content/uploads/2017/07/Basics-passive-income-Facebook.jpg

4) Treat Passive Income Like A Game. The only real way to begin your multiple passive income journey is when you are making active income. The initial funding has to come from somewhere. Hence, treat passive income as a game that has various levels. If you fail to achieve one level, it’s not the end of the world since you still have active income and can restart. Furthermore, a game is meant to be played with integrity. Using shortcuts (non passive income streams), someone else’s income as a supplement (spouse), or one-offs (capital gains) does not count. The primary purpose of any game is to bring enjoyment to the player and beat the boss.
You are also free to choose a fund that is based on any index that you want. For example, there are index funds set up for just about every market sector there is — energy, precious metals, banking, emerging markets — you name it. All you have to do is decide that you want to participate, then contribute money and sit back and relax. Your stock portfolio will then be on automatic pilot.
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. 
What if there was a way for you to effectively make money while you sleep? Sounds like a dream come true, right? Even for the biggest workaholics, there are only so many hours in a day. If only you could get paid multiple times for something you did once—that’s exactly how passive income works! Thanks to technology, the potential to create multiple income streams is even easier than ever before. We’re no longer held back by the limitations of a traditional 9-to-5 job, and financial freedom is at our fingertips. Even if you already work a full-time job you can still improve your financial health with passive income.
Do you want to earn $100, $1000 — or even more — on the side? You can start earning extra income today with the help of this list of ideas I’ve put together. Spend an hour or two each day working on items that are practical for you, and you can build alternative income sources to help you improve your financial situation  While many of the items on this list are passive income ideas, not all of them are. Some items require you to actively work for success.
A) Live, breathe, eat, and sleep this activity that is their passion. It's what they most care about. There's no way they'd give up this active, creative endeavor for a life of reclining on a beach chair. They cannot wait to wake up another day and spend another full day, from dawn to dusk, engaging in this project, building and creating things within this realm, giving this gift to the world. And, my guess is these people...
Can you expound on the use of publicly-traded REITs as a passive income source? I’m 31 years old. No children. No wife. No dependents. (I am the closest thing to Ebenezer Scrooge you’ll ever see). My monthly expenses amount to less than $2,000 per month (most of which go to pay student loans) . I have a decent job making over $55K per year. I also have a $60K inheritance coming my way in a few weeks. I am absolutely crazy about achieving absolute financial independence, which for me would require a passive income of over $2000/month to cover my living expenses. I could achieve that in a mere couple of years if I were to save excessively and dump my savings (and inheritance) into a Mortgage REIT via the stock market, most of which are shelling out above 10% returns in dividend payments. Is this a good strategy for me? Or am I being too hasty and assuming too much risk?
Do you have stuff in your basement, attic or garage that's collecting dust? If you do, pack up the SUV or car and kids and go to a flea market. You could make a couple of hundred, even thousands, of dollars, depending on what you're selling. You'll want to go to flea markets every weekend or at least every other weekend. Make an event out of it, and show your kids how easy it is to earn money selling their stuff.

Ebooks are one of my favorite sources of passive income. Now, you can do this the simple way and just publish it on Amazon's KDP. Or, you can go all out and build yourself a book funnel. Book funnels are powerful, but they won't be fully passive. For example, if you do a free-plus-shipping offer for your ebook (converting it into a physical book), you'll need to create some one-time offers (i.e. extra training) and up-sells (i.e. an audiobook). But, a book funnel can be very powerful.
When I started building my architecture-related business in 2008, I made my first dollar through advertising. I’d spent a lot of time and money building the site and getting traffic. Then one day I threw an ad on the site one day, and I made $1.18. Sure, I could find that much under my couch cushions—but that’s not the point! The point is that I was able to build something online, put an ad up, and make money without having to do anything. I learned it was possible, and it motivated me to move forward.
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