It seems to me that coming out positive with investing is extremely simple and easy if a person is patient, methodical, and not bent on making large gains in single transactions. A simple example would be to put $10,000 in a brokerage account, dump all of it into a broad market index fund any time the dow dips 1000 points lower than the maximum it's been at in the previous 90 days, then sell it all when the dow gets back up 1000 points as it will inevitably do. Such a strategy will not produce enormous gains, but it will produce gains of ~5% several times per year (on average) and will NEVER fail unless the entire US economy goes under. Even in a crash such as the 2008 housing bubble, you would not lose any money if you simply left your money in weathering the dip until the market rose back up. You would not make any money over this several year period, but you wouldn't lose any either. It's simple.
Why don't people understand this?