If you’d prefer to skip the startup phase, you might want to buy a blog that’s already built and earning revenue. This is actually pretty easy to do as a lot of people start blogs, and then get bored with them. Getting a blog going is a labor-intensive process, and it’s not uncommon for people to give up before they’ve reached their full potential.
Amazing that you saved between 50% to 75% living in NYC…I think that is one thing holding me back…the cost of living here. I’d like to invest in real estate, but I can barely afford to buy a place to live. I don’t need a large income to be happy, but I probably do need an income to support living in NYC as we don’t plan on leaving. The only thing I’m doing at the moment is saving in my 401K, IRA and a I dabble in stocks and P2P lending.

Your money is either in charge of you or you’re in charge of it, there’s no middle ground. Using some type of personal finance software can help alleviate some of that money stress and better allow you to manage your money effectively. Without it, you may just be setting yourself up for constant financial worry. Life is already tough enough and there’s no need to make it more difficult by simply hoping your money issues will all work out in your favor. Hint: they won’t.
Which all goes back to my point – since companies change in a lot of unpredictable ways, it makes more sense for passive income to just ride the market by investing in a Total Domestic Stock Market, Total Bond Market, and Total International index funds, with allocations that depend on your goals and time horizon. For income, withdraw 4% or less, depending on what research you believe, and you’ve got a pretty low risk strategy.

Generating passive income requires upfront work. Some say achieving passive income is actually quite an active pursuit. Some paths may be. But then they may not be truly passive income investments. Acquiring a passive income producing investment can be very simple, even if there are many others behind the scenes doing a lot of work to vet, package, and manage that investment.

The U.S. Internal Revenue Service categorizes income into three broad types, active income, passive income, and portfolio income.[1] It defines passive income as only coming from two sources: rental activity or "trade or business activities in which you do not materially participate."[2][3] Other financial and government institutions also recognize it as an income obtained as a result of capital growth or in relation to negative gearing. Passive income is usually taxable.
While it is important to find something that you love to do and turn it into a money making business, you do have to be cognizant of the return as you pointed out. There are many opportunities that I found and tried out that at the time seemed great. But when I took a step back, I realized that I was working a lot for very little income whereas other things I love doing brought in much more money.
Some people take it automated well before the year is up. When it converts, it converts. If you target the right people and you're able to create the right message that appeals to your audience, you might just hit a home run. An automated webinar often involves the creation of a webinar funnel. That includes, not only the webinar, but also the email sequences, and possibly a self-liquidating offer, and maybe some done-for-your services and up-sells.
Residual income is money that is earned on a recurring basis, typically as the result of a single original action. Rather than earning an hourly wage, residual income is typically generated through an initial investment of time or money with the goal of earning continuous payments. Once the initial investment, product, or service is made, the ongoing income that is earned is generally passive in nature.