I don't understand why Wisconsin is supposed to be not naturally favorable turf for Trump. Could someone spell it out for me?
It's full of communitarian upper midwestern 'good governance' types who like people who are nice and don't like people who are brash. The Republican demographics tend to be more on the upper socio-economic status end of things in Wisconsin as well. The Wisconsin union voters tend to be more Democratic than in other midwestern states.
This.
There are definitely pockets where Trump will do exceedingly well, but again, it will depend so much on turnout. I don't think Trump will do well in Ryan's stomping grounds, and there just happen to be a lot more people there than in the rural areas. But then they are also going to be less fired up to vote, I think.