I think Ron Jon has seriously damaged himself now in places like De Pere, Neenah, and Greenfield. He’s blatant kissing up to Trump probably has hurt him in the inner ring Milwaukee burbs and Green Bay.
As for why Baldwin did pretty well in 2018, the main reason? She knows dairy issues really well. My in-laws live in Sheboygan County and there are multiple cheese plants in Calumet, Sheboygan, and Manitowoc Counties chalk full of deep red voters. Baldwin has always reached out to them to help and a lot of the farmers were truly grateful. Baldwin did really well in places like Plymouth (The Cheese Capital).
Would you say the chance is above 50% that he would lose against a decent Democrat in a neutral environment (something between 2002 and 2018).