He would do better to hit her on Benghazi or emails or international policy failures while she was Secretary of State. Those would be far more effective and he barely touched on them in the first debate.
And immigration too. Of course Holt didn’t bring it up, but Trump could have brought it more into the discussion of the economy and wages.
Also, when Trump recently made the very obvious, common sense statement that no foreigner has a right of immigration to the United States, Hillary’s official Twitter page responded with “We disagree”, which can only be taken as meaning Hillary things foreigners do have a right to immigrate, which is a radical, extreme view if ever there was one.
Combine that with Hillary’s radical support for increasing Syrian refugees by 500%, plus her support for massively increasing overall legal immigration, and her announcement that the only way her administration would deport an illegal alien is if they murder or rape someone, and Trump has lots of easy targets on immigration. On all of these points Hillary is pushing positions that most Americans oppose, but of course the media will not report that. And there is no chance at all that a question will make it through that is crafted to make Hillary explain her radical positions, and there is no chance that a moderator will put a follow-up question to Hillary along those lines. So Trump will have to make these points and put her on the defensive about them. They’d be more effective, I think, than talking about building the beautiful wall and making Mexico pay for it.
I just don’t think Trump can finesse an attack with regards to Bill Clinton’s predatory nature to show Hillary as an enabler. It’s a high risk strategy, with questionable reward.