You are ignoring the Liberal Mantra, "Liberals are smarter than you are; conservatives are simply uneducated liberals". They honestly believe, with all their being that they are more educated, more sophisticated and more enlightened than the great unwashed.
Liberals will be the first to tell you that "if you truly understood the situation", you too would be a liberal. So, how do they approach this? Get a hilariously funny liberal (Al Franken is certainly a massive failure here) and as soon as the public learns the 'truth' of Liberalism, their investment will displace Rush, Hannity and the others. And I'm telling you, this is a HUGE financial market they are going after.
Given the very poor financial shape of the Democratic party, they can't afford to spend this money on radio solely to promote their ideas, without a huge cash reserve .... unless this is their way around the McCain bill which limits speech during the voting season.
1) It is not financed by the Dem party, but by liberals, who are limited in how much they can give directly to the party.
2) I already advocated that this is their way around CFR. It is a giant paid attack ad that will run right through the 60 day blackout period.