I'd say two of those were objectively bad -- the war and giving up freedoms for security. The unwillingness to enforce immigration laws was bad unrelated to automation. The others are more equivocal, and, though I know it is not popular in these parts, I would say that there is still a lot of net positive in offshoring.
I know a number of people who have had dealings with Glenn Greenwald. My understanding is that he is a snake, but this is a marriage of convenience. And on your list of candidates, also unpopularly, Romney is the only one that was an easy vote for me. I should point out that even as a Senator, while he voted twice for impeachment for Trump, those were not important votes because they were not marginal votes. When faced with important votes, he has been solid.
That is all I have to say on the subject.