I have not. While I am intrigued with the possibility of making online income, it seems to be less passive then how I want to spend my time. Regarding your blog / site, you have done quite well for yourself. However, you have to keep pumping out content or your site would eventually go out of business. That sounds like more of a commitment then I would want. Regarding your book sales, it is probably relatively passive now, but certainly was not when you were writing the book. Now if you love it, great. Just not for me.

1. The batting cage idea is very risky. I’ve seen many of them close over the years and it is not anything close to passive income if you want to keep the business going. You have to continually promote it and target youth leagues, coaches, schools etc to catch all of the new players who grow up and want to play. I’ve played at probably 8 batting cages over the years and 7 of them closed.
I love my passive income. When you achieve enough of it the decision to start slowing down is easy. My passive income is plain vanilla. It is just coming from stocks and muni bonds. Some complain about the tax drag of income in a taxable account but I look at it as covering my living expenses in retirement. Interestingly I have never invested in “income” producing funds etc. If you save enough your portfolio will pay you more than enough without doing anything exotic.
Because passive investors’ rentals are viewed as secondary income, they can only deduct the normal costs associated with their rental properties. They cannot deduct any home office expenses and are limited on how much they can deduct from any losses they might incur. As of 2010, you can only deduct up to $3,000 from your other active income like your job or employment.
If you make the choice, it is binding for the tax year you make it and for any later year that you are a real estate professional. This is true even if you aren’t a real estate professional in any intervening year. (For that year, the exception for real estate professionals won’t apply in determining whether your activity is subject to the passive activity rules.)

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).

Investing in a business: Another good way to generate passive income is to invest in a business --even a small one -- in return for a percentage of the profits - just like Shark Tank, only smaller. Lending $10,000 to a local business that, for example, is working on a mobile app for Apple phones could lead to a passive income-generated share of the profits when that mobile app starts selling like hot cakes.
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.
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