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If it were me, I would fully-fund the ROTH IRA on day one of 2007 if I could. You'll most likely pay less per share if you buy it as early as possible.
Would I buy that specific TIAA-CREF fund? Probably not. Small caps are a bit too risky right now.
Keep up the great work on the blog!
But remember... Buying it all on Jan. 2 of every year is still dollar cost averaging, just with less granularity. In this case, you'd be averaging across yearly instead of monthly purchases.
And keep in mind that, as with any risk aversion strategy, you will (on average) lose out on earnings... The market trends upward (on average), so in all likelihood it will be cost more later.
All that said, I think that dumping it into a money market in the Roth and then doing DCA from there is probably what we'll end up doing.
Just something to keep in mind but otherwise I'm all for contributing in a lump sum at the beginning of the year.
Realistically it probably doesn't matter that much as if you are leaving it in there for 30 or more years the possible loss by not DCA is probably not that great, but I found I often invested it slowly throughout the year anyway so now this year I'm only going to deposit like $2k every couple months until I get to $8k.
I wouldn't worry about DCA either. Just make sure you max out the contributions every year. If paying a lump sum is the easiest way for you and your family, then by all means carry on.
I would also suggest investing in a foreign small cap fund for 2007.
The market looks so scary right now that I'm not buying a single American stock in 2007.
A bearish market is coming. Do some research on foreign funds, and diversify your risk overseas as well as sector-wise.