re: At how many years prior to retirement do you...

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Math is math and has no expiration date. Any percentage you give to someone else is not allowed to be compounded for yourself. That equates to a lot of money. Someone already mentioned the Frontline episode "The Retirement Gamble" which goes into more detail if you're interested. Bottom line is that you can manage the risk yourself and the fact that you're not giving away a percentage means you buy yourself a lot of leeway to not get it exactly right. Having said that, it's not difficult at all to do.

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Math is math, and the average person is really stupid. Vanguard Target Date funds are currently charging a fee of 0.15%. Can you save a bit of money by educating yourself and handling your investments on your own? Absolutely. But would the average person likely come out way ahead if they just plugged away at a target date fund and did their best to forget it existed? I firmly believe so, yes.