If you need cash flow, and the dividend doesn’t meet your needs, sell a little appreciated stock. (or keep a CD ladder rolling and leave your stock alone). At the risk of repeating myself, whether you take cash out of your portfolio in the form of “rent”, dividend, interest, cap gain, laddered CD…., etc. The arithmetic doesn’t change. You are still taking cash out of your portfolio. I’m just pointing out that we shouldn’t let the tail wag the dog. IOW, the primary goal is to grow the long term value of your portfolio, after tax. Period. All other goals are secondary.

Diversify safely but DIVERSITY. You do not need to get the best and highest return all the time. If so, you are not earning passive income you are earning active income which is taxed differently (see IRS.GOV passive -vs- active income definitions). As an investor you do not need to be chasing ‘the almighty dollar’. This is a losing proposition. Make the dollar come to you.
The vast majority of my investing is in retirement accounts and won't be tapped for income until I reach at least 59.5 years old. However, I have a very small taxable investing portfolio (less than $5k) with Ally Invest where I invest in a handful of stocks that I value. I do not use the earnings as income – I simply hold these stocks. But I have an unrealized gain of $340 from this year so far.
I also noticed that in your passive income chart at the bottom that you don’t include your internet income other than sales from your book. Is there a reason for that? Do you not consider is passive because you are actively blogging all the time to create it? Or do you just not want readers to know how much money you generate from blogging activities?

There are many people who get paid vast amounts of money to become the CEO of a company, play professional sports, or star in a movie. Earning a high active income is often a lot of hard work and requires a dedication beyond most of us. It’s also limited because no matter how much money you get paid you still need to show up to work to earn your money.


After these tenants move out, I'm thinking of just keeping the rental empty with furniture. It sounds stupid to give up $4,200 a month, but I really hate dealing with the homeowner association, move-in/move-out rules, and maintenance issues. Given that the condo doesn't have a mortgage and I have to pay taxes on some of the rental income, I'm not giving up that much. The condo can be a place for my sister, parents, or in-laws to crash when they want to stay in SF for longer than a week or two.
Leveraging the internet to create, connect, and sell is something every creative person should attempt to do. The only risk is lost time and a wounded ego. You can start a site like mine for as little as $2.95 a month with Bluehost and go from there. They give you a free domain name for a year. Forget all the add-ons. Not a day goes by that I’m not grateful for my site.
My favorite type of semi-passive income was rental property because it was a tangible asset that provided reliable income. As I grew older, my interest in rental property waned because I no longer had the patience and time to deal with maintenance issues and tenants. Online real estate became more attractive, along with tax-free municipal-bond income once rates started to rise.
While some have degraded the meaning of passive income with cheesy ,get-rich-quick type schemes, it doesn’t mean getting something for nothing. Whether it is investing hard earned capital, sweat, time, or providing a service such as housing, there is a lot given to create passive income. Each party provides something of high value, even if the end product means simply buying income property.

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