I don’t follow BOR much, but he seems to me to be a kind of traditional “Reagan Democrat” who will go for populist economic policies most of the time, leaning left, but wants a strong defense and still holds somewhat more traditional values and so is uncomfortable with the sheer depravity of so much of the Demagogic Party. Thus, a Ronald Reagan can win his vote for the Republican column, especially against weasels like Carter and Mondale, but most times he will vote for the Demagogues.
Ditto to everything you said about him, plus he has that Harvard exposure which I believe made him feel out of place because of some of the “stuffy” traditional values he grew up with, but nevertheless, desirous of being part of the elite.