the very first person Damore engaged after his firing was Stefan Molyneux, who is undeniably alt-right.I try to avoid Molyneux as much as possible. Keep in mind that the term "alt-right" is overloaded terminology. Roaming Millenial has a video where she outlines 4 broad categories of "alt-right." Not all of them are White Supremacist. Molyneux, I would just categorize as a very cultish Libertarian. Molyneaux should be rejected because of observations of his actual morality, with regards to questions of free inquiry. You might know additional bad things about him. However, it's "insipid" (your word) to judge James Damore's ideas based on association.
It's also insipid to suggest that being gay or Jewish precludes being alt-right
Just as insipid to put Gad Saad, Dave Rubin, and Steven Pinker into that category, based on what they say and the positions they take. The fact that they are gay or Jewish should at least get you to question the narratives pushed by media and take into account their actual positions. Hint: The narratives with regards to those 3 are false, and are unprincipled attempts to silence through association, probably because the critiques and information they supply pretty much demolish those narratives.
What would that make Milo Yiannopoulos?
Milo is, as far as I can tell, genuinely is anti Alt-Right, where that term encompasses the more radical 3/4ths of Roaming Millenial's categorization. He may well line up politically with some segment of the online community which rejects identity politics, but which is still far right. He also displays a problematic morality as evidenced by some of his actions. In my estimation, he's half activist and half opportunist.