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.

There are many ways to get people onto your list. Lead magnets are one such resource. For example, you can build ebooks, checklists and cheat sheets. But you can also do content upgrades, such as PDF versions of an article with added resources in them, four-part video training series, and more. Think about your audience and what you can offer them to better serve them, then treat them with some respect and you'll eventually reap the rewards.
Personally, my experience with Amazon thus far has been good - a few of my short eBooks generate steady passive income on weekly basis with zero additional effort from my side. One thing to note though - Amazon pays 70% royalty on each eBook sold only if your eBook is priced between $2.99 to $9.99. Less than or higher than that pricing structure, the royalty decreases to 35%.of your book’s listed price.
It's important to keep in mind that participants don't "qualify" for all surveys. Market researchers often want opinions from users who match specific demographics or who are in-market for particular products and services. If you attempt a survey that you ultimately don't qualify for, Swagbucks will give you at least one point in its rewards program. You know what they say: "A penny for your thoughts".
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.
Using Fiverr is a great way to pick up work. Once you have signed up you can advertise your services. Fiver allows you to create your own gigs, whether you are offering web design, digital marketing, writing, or something else. You can choose how much you want to charge (it can be more than a fiver) and people will then contact you if they are interested in working with you. Fiverr will not only help you get experience if you are just starting off as a freelancer, but it will also help you earn some extra cash.
I will share what we did, because it’s an incredible success story. We used an existing tax loophole where if you sell your primary residence (after having lived there at least two years) you get to keep your profit tax-free. So, we stair-stepped. We bought house after house, at least two years apart, used the profit money to pay down on the next house (so on and so forth, yadda yadda) building up equity as we went along… and now, we own a $600,000 house debt-free. And now we are using our paid-off home as leverage to borrow money to buy commercial buildings to rent out. I like commercial because it’s a BUSINESS transaction… kids, pets, other wear and tear that you see with residential rentals is nonexistent. People take care of their business space much better than residential. You have to be in a good area for renting out commercial – a thriving business community – to make this work. But that’s how we “made it”, and though it took 15 years, we will have residual income to take care of us when we’re old enough to retire. People made fun of us for moving so much, but who’s laughing now? 😉 Oh, and our child only had to change schools once (and we wanted to anyway) because we stayed in the same general area as we moved around. We were careful not to disrupt his life too much.
That said, lot's of people are making extra money by publishing their own books on Amazon.  For instance, my friend Bob published a few books on Amazon on how to make money blogging and has done very well.  The first book provided basic tips for a small price, but his next book, Pro-Blogging Secrets, is offered at a premium price and he also has an online course.
The takeaway: As you seek out creative ways to earn more money this month, remember that not all apps and methods are the best match for you. Keep in mind that side hustle apps, such as Uber, Rover and Airbnb will take a percentage of your booking fees and that you will be treated as an independent contractor, not an employee, which may have its challenges. Recently, Instacart, a delivery app, received backlash when workers determined that their tips weren't being appropriately added to their earnings after a tweak to the reimbursement system.
I’ve never invested in real estate (except to live in), but am always intrigued by communities like FS who seem to have such a passion for it. My intrigue stems back to my earlier comments that the long term trends in appreciation in real estate are simply not very competitive versus equities, despite what Robert Kiyosaki had to say in his book, Rich Dad, Poor Dad.

Are you seeing the possibilities here?  Think about what book, or series of books you could write to help people in your field of expertise?  You might start with an eBook offered on your own website that covers the basics.  Use the eBook as an opportunity to tell people about your more in-depth book on Amazon and finally, follow through with an advanced book offering.
I have a personal blog that I use for journaling. I became good enough that I opened my own business as a social media consultant. I’m now making a decent amount of extra money. I am also a photographer with a lot of graphics program experience, so I make a little more by doing graphic design, photography, and even digital enhancement. You don’t have to be the best at something in order for it to be profitable; you just have to put in the work and be better or cheaper than other people out there. However, it IS work.
A fitness site can have numerous revenue streams. Create healthy eating plans and recipes and lock them away as premium content. Promote and sell a fitness training course, eBook, or a series of videos. Or advertise your own personal fitness services on your site. Topfithub is a good example of a fitness site with decent video content alongside product reviews.
Upwork: This website offers a great marketplace for selling just about any professional service. You don't need a merchant account, website of your own or anything else for that matter. All you need to do is be able to provide a high-quality service at a reasonable price. But be informed, you will have to compete with many others that are constantly bidding on open jobs. 
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