Playing both sides of the street is a brilliant way to get hit by traffic going both ways.
That's really not a joke either. Everything I've heard about the people at Trump rallies has been that immigration is their biggest motivation. The most virulent hardline anti-immigration are of course from the border states of Iowa (such as Steve King) and Wisconsin (if you can remember former Congressman Jim Sensenbrenner). [/s]
Trump needs to win white people who voted Obama and are disgusted with our current immigration and terrorism "problems," while appealing to a broader audience of independents. This is not possible, and is why he will lose.
Meanwhile, I hope you don't mean the the general populations of WI and IA are anti-immigration. I'm from WI and this has not been my experience at all. Green Bay for instance has been excellent in welcoming Hmong families, and Mexican immigrants are able to integrate with minimal drama. Conservative Catholics make up a large portion of the Republican base, and they are good about welcoming immigrants into their parishes.