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You forgot to add:
-Everyone else is trying to do the same thing, so look at your actually expected real rate of return on all this saving you're planning (negative even before taxes on withdrawls or dividends, over the last 10 years, and with high volatility), and then hang your head and ask why you even bother.
I bring this up because I save a lot and use the tax-advantaged options, but when I look at the numbers, I have to ask, what's the point? After taxes (which will have to go up as the tidal wave of unfunded obligations comes due) and inflation, you barely get anything out of saving. (Yes, there's the no-tax Roth, but you get to invest very little in it.) Plus, if you save it for long enough not to be penalized on withdrawl, you have to put off consumption until waaaaay into the future, when it will do less for you.
It just seems like you'd be better off buying durable assets or investing in marketable job skills, which are more robust against the kinds of things that punish your savings.
I've been exploiring the "infinite banking" option: mutual universal whole life insurance that you can borrow against and which gets a steady, relatively high rate of return and is tax-shielded and has a long pedigree. Seems a lot better than following the herding into IRAs which will probably have their promises violated at some point.
As Rain said, asset allocation is important. The standard advice to put most of your savings in low cost index funds has the merit of simplicity and is not bad advice for most people but it is possible to do better by having a bit more diversification than that implies. Rain suggests a percentage allocated to int... (read more)