The psychobabble is a little dispiriting. Still, the bit about the Democrats being a party of capital who sort-of have to pretend not to be is basically true, and yes that issue probably does explain some of the problems with communication that party figures sometimes have. Not sure if it really explains Obama's battery powered corpse act though.
One of the most annoying things that I found about the psychobabble is that it doesn't even seem to come from a good place. He is basically saying Obama is some noveau riche, Jay Gatsby figure who
desperately wants to be accepted by the old money types. Who knows, maybe this is what helped his Yale cohorts boost their self esteem back in the day. 'They want to be us'. It implies further that the people who really can make a difference to 'fight the power' come from this class, in this case FDR. Similar, unmerited, themes are used for civil rights too; i.e., that it took a Southern racist like Johnson to get passed etc. etc.
I agree with his analysis about the party. And I think you can find plenty of cases of massive contradictions and hypocrisy. Alas, this is the fundamental flaw of our cherished two party system.