When I purchase an existing online business, I look for cash flow over the past year and where the money comes from. I want the sources to be more passive so that it does not take a lot of my time. Also, typically I will make an offer that is 18 – 24 months of profit so that I know that I will get my money back within the next two years. I hope that helps!
You need to decide which machines you want to run, get the necessary licenses to operate them (you're selling items so you need to get sales licenses and whatnot from your state), buy the machines and a truck for the items in the machines, find a supplier of the products, and then finally you can secure locations. Finally, you need to service them periodically or hire someone to service them.

One of the things I'm surprised your article doesn't mention is the tax advantages of this type of investment. The depreciation and rehab costs (purchasing distressed properties) can be huge deductions to ones income taxes, which none of the others have. Then, along with the appreciation of real estate, this passive income investment outperforms the notion of maxing out my 401k as well.
Also, if you pursue an income stream like affiliate marketing, your blog can be a source of content that allows you to link to affiliate sites in a way that is seamless and natural. For example, if you are an affiliate marketer for a company that sells productivity tools, you can blog about your own struggles to stay on top of your to do list. Then, you can mention how much those tools have helped you.
A perfect example of the Active Problem Solving + Automation concept is in my online courses I’ve created over the years, or my free webinars I’ve created more recently Each of my online courses and webinars are targeted to help people with specific problems, whether that’s in the area of affiliate marketing, podcasting, building a brand, and so forth. I am always improving upon the courses, but they are also evergreen for my audience.
One aspect you might want to add to your scoring is “inflation protection”. At one end, bonds and CDs generally pay a fixed nominal coupon that doesn’t rise with inflation. Stock dividends and Real estate rents (and underlying property value) tend to. Not reallly sure how P2P lending ranks- though I suppose the timeframes are fairly short (1 year or less?) and therefore the interest you receive takes into account the current risk free rate + a premium for your risk. Now that I think about it, P2P lending probably deserves a lower score in the activity column than bonds too (since you probably need to make new loans more often).
And real estate does more than just track inflation – it throws off income (which is important to some people and useful to most). And while your underlying asset is appreciating, the income also grows as rents increase over time. And if you make smart and well-timed purchases, both rents and asset values can increase at well above the rate of inflation.
I actually spent a year and a half working as an affiliate marketer (mostly selling drumming related products – lessons, kits ect). 5 years on and one of my one page sites (which I’ve not touched) still nets me about $150 a month. I won’t be retiring off that but only really now appreciate the reverse pyramid approach to entrepreneurship (working for nothing initially but later being paid without effort!)

We usually think of Craigslist as a place to buy and trade random stuff, but Craigslist can actually be a great opportunity to sell your services online to an active and engaged audience. Simply check the “jobs” section and “gigs” section for specific cities and see if anything matches your skills. The great thing about Craigslist is that it is one of the highest converting traffic sources on the internet (think active buyers) which can mean more opportunities at higher pay.
That strategy seems waaaayyyy less risky than actively picking stocks of supposedly “reliable” stocks that issue dividends, which could be cut at any time due to shifting industry trends and company performance. Dividend investing feels like an overly complex old-school way of investing that doesn’t have a very strong intellectual basis compared to index investing.
So, armed with my real estate license and this desire to help physicians (and create a business at the same time), I started a real estate company called Curbside Real Estate. My goal was to help physicians buy and sell homes by connecting them to trusted realtors and lenders. It started organically, largely through word of mouth. Next thing you know, I was helping doctors from coast to coast. The business was great and I felt I was making an impact helping physicians, but I still wanted to own my own real estate investment properties.
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.
A business factoring company that seamlessly integrates with a particular sales-tracking software and provides real-time distribution of commissions. You would need to find a factoring company or an investor who specializes in funding direct-response companies, a risk analyst to audit risk associated with each sale within a company, and a third-party payment verification service.
If you have specialized knowledge in a certain topic, you can put together an online course to teach others. For example, if you have experience in real estate investing, you can create an online course “Real Estate Investing 101”. The benefit of an online course is that once you create the course material, you can sell it to as many people as you want.