Lump sum vs dollar cost averaging

Since I chose to roll over my IRA into a stock trading account in January, I opted to buy a little at a time. This fortunately saved me from a massive drop during January and February. I suppose it simply depends on the timing.

Mymoneyblog.com had some interesting viewpoints on this. I had around $150,000 rolled into my IRA account. Here's my exception to the rule.

Beginning January 03, 2008, the S&P 500 ended at 1447.16. That's when I started purchasing stock in small bites. Throughout January, as the S&P 500 slid down to 1350 on January 22, I continued to add to my positions, averaging my initial costs down. So my IRA has a +4.44% gain year-to-date while the S&P 500 is currently sitting at -10.03% year-to-date. My previous blog entry was higher, but it got hit hard on Friday.

I'm curious though, if there is any software that can track my stock purchases versus an equal dollar cost of the S&P 500 for each of my stock transactions. Because as it stands, I believe most tracking software compares your portfolio against the S&P 500 as a single transaction from the start date of comparison, though there may have been multiple periods between where you may have purchased stock. That way I'd be more fair, because there are certainly some dips in the S&P 500 down to the 1273 and 1276 on separate days this year that would have come out to be gains as well.