I think it was harder to narrowly categorize those as in-group vs. out-group than the newer ones though.

Maybe it's because people are more polarized now and there's less room for talking about interesting points that don't clearly fit into an existing political group? Maybe if those were written today people would find them similarly 'disconnected'?

I don't know, but I agree his new stuff isn't that different from the kinds of topics he's historically written about.