As FishOutOfWater suggest, I bet they're going for the big, easy money, and that Doolittle et. el. will be transferring money to competitive districts. Strategically, it's not a bad idea, especially as W becomes increasingly radioactive.
This ad actually leaves me a little flat. There are repetitions of the same shots to no rhetorical effect. It started off well enough, with the 'standing up to Bush' line, but it's not really possible for Lamont to coopt that message as uniuely his in the same way Dean did grassroots populism, which one could say he (re)created. It would have been more effective if he had continued the thrust of the opening and shown how others (wink wink) have NOT stood up to Bush and how he is going to.
When he holds up the picture of his daughter, it's reminiscent of the parents of victims doing the same, which always leads to the viewer identification 'that could have been my daughter!' Only here we are led to identify with the man and agree 'How could I look my daughter in the face and say I support Sherwood?' I think it's an effective ad.
If it is a group of angry young voters who produced this, then it's authenticity holds. However, if this were to prove to be a product of 'big guns' -- a Swift Boat sort of thing -- then it would lose that value. Tighter message, etc., would then become more important.