Obama's policies were pretty Clintonian.

Democrats have two big problems with swing voters. Well, three, but two are self-inflicted. The first one is that they are explicitly race-conscious. Biden's up-front announcement that he would appoint a black woman to SCOTUS is an example. That creates a question in some voter's minds: is the appointee the best person for the seat at that particular time, or is she being appointed because she is black and has the right political views? Dems talk about race, ethnicity and sexual orientation as if it is relevant to the job--they tend to lead the candidate descriptions with 'the first woman," the first openly lesbian..." etc. It is annoying and counterproductive. They don't need to change who they nominate--but they should not add a candidates minority status to the list of reasons voters should support the candidate. When Republicans choose a minority, they just choose and let the choice speak for itself.

The second thing they do is let the progressive wing of the party push them around. The left wing of the Democratic party is simply not popular enough with the electorate to carry statewide or national races. I don't know why the forgive student loans crowd can't understand that when you are only 30% of the Dem coalition, you aren't going to get your way.

The third thing isn't self inflicted---it's the Fox and Facebook effect. The left doesn't have the equivalent media ecosystem. Some Dems get it and will engage with Fox, but a lot of them refuse to and that hurts them. Showing up on Fox where conservative voters can see your face, hear you talk, and assess you for themselves is really important.