I would actually consider this some sterling and reasonable analysis if I could ever once recall you attacking Hillary for her hypocrisy of making a campaign issue of being "with" women that have been sexually assaulted and claiming that they should be believed to be speaking truthfully when making such claims, considering her part in defending her husband continually from people making such accusations towards him in the 90's.
As it relates to strategy and the potential hypocrisy of such things, it's a fair point in the notion that it could potentially harm Trumps ability to attack based on that. On the flip side, as we've seen repeatedly, conventional wisdom hasn't seemingly stopped the damage Trumps attacks have managed to do. I imagine that his attacks on Clinton will not be aimed at making her unlikable on a personal level, but rather to try and destabilize the ground she stands on in terms of her attempts to proclaim herself as someone who advocates for and is here to defend women. As was the case in some of the Republican primaries, Trump being an asshole doesn't mean that the sly point he's trying to put across doesn't implant itself well. And, unlike most politicians I've ever seen, Trump has shown an ability to garner support DESPITE being viewed as an asshole by those voting for him.
As it relates to the pick of Newt himself, frankly I like it. I'd prefer a governor so you had some actual government executive experience, but I see the point in not going that route if they're going to hype his business experience as what's really "needed" for the country in terms of the "chief executive". As such, a strong legislative / policy VP would make sense. Newt doesn't particularly help him with any swing state, but he does perhaps help him with some of those disaffected Republicans who are normally solid assumptions to be part of the voting base that were considering sitting out. Trump has shown himself to pull out Republican voters that had took their ball and gone home in previous years (The very thing they attack people for considering now, ironically enough), so a pick that shores up some of the ones that would be taking those peoples place could help.
All told, I think Newt would be a solid, if not spectacular, pick.
