For those of you who don’t want to come up with a $220,000 downpayment and a $900,000 mortgage to buy the median home in SF or NYC, who don’t want to deal with tenants or remodeling, and who wants to not do any work after the investment is made, check out Fundrise. They are my favorite real estate crowdsourcing company founded in 2012 and based in Washington DC. They are pioneers in the eREIT product offering and they’re raising an Opportunity Fund to take advantage of new tax favorable laws.
Investing in real estate has been around for ages.  Whether you are looking to buy your first duplex or getting into a large commercial property, rental properties can provide passive income through rents with some very appealing tax benefits.  This method can be harder to get started with given the initial capital needed in most cases, but is certainly a great way to generate passive income.
When a taxpayer records a loss on a passive activity, only passive activity profits can have their deductions offset instead of the income as a whole. It would be considered prudent for a person to ensure all the passive activities were classified that way so they can make the most of the tax deduction. These deductions are allocated for the next tax year and are applied in a reasonable manner that takes into account the next year's earnings or losses.

Thanks for asking. https://passiveincomemd.com/what-is-passive-income/ gives a good summary of the definition I use. But in brief, it’s income that isn’t proportional to the time you physically put into acquiring it. It doesn’t mean it’s not without work or effort. It’s just that most of the work is done up front and it continues to pay off long after that initial effort. Real estate fits into that box. There’s definitely a spectrum but compared to what we do as doctors, where our compensation is directly linked to our time, most of these things are quite passive.
If you are not a real estate professional but oversee your rental real estate, your revenue qualifies as a different type of passive income and you might be able to claim a portion of any losses against active income. As of the 2018 tax season, you can write off up to $25,000 a year in rental real estate losses if your Adjusted Gross Income is $100,000 or less. If your AGI is over the threshold, the size of the loss you can claim goes down by 50 cents for every dollar of income. At an AGI of $150,000, you no longer can take the passive loss against other income.
Passive income is definitely the goal and I think you hit it on the head with the point about upfront work. That actually coincides well with most physician careers. Work hard like a resident and spend like a resident to build up an investment portfolio right away while you are young and full of piss and vinegar. It then has time to grow and be there for you as you need or want to slow down because of aging or kids etc. Plant the seeds early and then live off the crops.
There’s stock and then there’s blue-chip stock. In poker, the blue chips are the most expensive. In the stock market, blue-chip stocks are considered more valuable and less risky than lower-priced stocks. These stocks belong to well-known companies like Facebook, Google, Johnson & Johnson, and so on. Due to the massive success of these corporations, they pay shareholders lucrative dividends. A single blue-chip stock can cost well over $500. If you can find the money, the quarterly or annual dividend payments would amount to generous passive income you can rely on. Though these stocks are considered more lucrative, all investments involve risk. Lehman Brothers’ stock was solidly blue- chip until the financial crises tanked the company. Keep that in mind when investing in this type of stock.  There are no guarantees in the stock market – only educated guesses.

According to Uncle Sam, you need to be "materially involved" in an enterprise to earn active income. With passive income, it's just the opposite, as the IRS deems you to be earning passive income if you're not materially involved with a profit-making enterprise. By and large, expect income to be taxable if you are engaged in a passive income enterprise. You will need to report earnings to the IRS.
I love real estate investing, but it requires a lot of upfront capital plus you are going to have to learn to love your tenants (see point 6 below)! Crowdfunded real estate investing gives you a way to still invest in the real estate market, without having to necessarily put in a lot of money upfront. It’s definitely a much more passive investment than owning a flat or a house!
If you or your spouse actively participated in a passive rental real estate activity, the amount of the passive activity loss that’s disallowed is decreased and you therefore can deduct up to $25,000 of loss from the activity from your nonpassive income. This special allowance is an exception to the general rule disallowing the passive activity loss. Similarly, you can offset credits from the activity against the tax on up to $25,000 of nonpassive income after taking into account any losses allowed under this exception.

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.

I am an English major and a herbalist with so many ideas and no extra income to fulfill them. I recently started renting my extra apartment in the attic with Airbnb. It’s amazing how fast I accumulated some money for few hours of work between guests. Now I want to persue all my dreams of opening an online herbal store, publishing my ebook of treating Ulcerative Colitis with herbs, blogs, and videos, and pretty much all of the ideas mentioned here. I will save this article as its really helpful for whomever needs some ideas…
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