IIRC, Rich never said "they're the same", he said that one is crazy, and the other is entitled. And that he refuses to play the "pick your poison" game. He refused to concede that one poison was objectively better than the other, because he feels like his vote is a positive endorsement, and he can't bring himself to support what he sees as poison.
He wasn't pro-Trump, he was anti-Hillary (in addition to being anti-Trump), so pushing a stronger anti-Trump message wouldn't do much to change his mind about Hillary (although I suppose it's possible, if the argument is extreme enough, although you run the risk of being ignored as hyperbolic). Trump had already lost Rich's vote.
Seems like the better way for someone with a time machine to secure Rich's support would be to ask Hillary to make at least one stop in Wisconsin, rather than ignoring the state because she expects to win it by a healthy margin.
Clearly going to the upper Midwest states multiple times would have been a smart move for the Clinton campaign (or at least removed that as a reason she lost). Does Hillary take the blame for not being a great candidate and running a bad campaign? Sure.
But that wasn't the point of Jack's tweet. He said "Candidates are often not perfect but they can add to a bigger picture. I'm hopeful that we can get over some of the petty bullshit from 2016." Whether Rich said "they're the same" or he said "Hillary is entitled", I'd call either argument petty bullshit. That petty bullshit (and the subsequent tweet about Wisconsin's redistricting maps) led to a Trump presidency and a Congress that isn't willing to prevent the cruelty we're seeing at the border. That's the "bigger picture".
I don't know about the Pre Rec streams because I never watch them (or pretty much anything Pre-Rec, to be fair). I'm relying on folks like you and Shy (who probably doesn't watch anymore, to be fair) to provide clarity and insight into what they say there. So if I'm misconstruing Rich's argument and it's more than (what I consider) petty bullshit, then my bad.
Another point: I'm really not trying to make this into a political thread, but I thought that, after the discussion on the last page or so, it would be worthwhile to post Jack's tweets. I think it also adds a little bit of color to his personality for those who don't watch the streams. It's pretty clear how Josh and Jack feel about these issues from their tweets, but it's harder to get a read on Mike (who, to my knowledge, doesn't tweet) and Jay (even though Jay is active on Twitter, I don't think I've ever seen him tweet politically...). And depending on whether you watch or don't watch the streams, Rich's take on this stuff.
So the whole fixation on SJWs in multiple videos makes it difficult to pick up on whether it's a joke or not, how sensitive they are to these things (not at all, apparently), and so on (like
firehawk12 said), because you don't know where they're coming from. Not that a joke can be bad or inappropriate if you have a specific worldview, but it tends to inform whether it was meant maliciously or just an ignorant goof.
So, yeah, that's my rant about things. Sorry for being so long winded. We can go back to bad movies now, if you'd like.