Wasn't Feingold himself basically from Madison? Or has the state moved so far to the right now that simply being from Madison will kill you?
Feingold was effectively from Madison. Being from Madison alone won't kill the Democrat's statewide chances but it won't help, especially given the sort of things necessary to get on top in the Madison area Democratic Party. Someone like Feingold would be more immune to that problem because he's been apart from Madison local politics for a long enough time that it wouldn't apply to him. For instance, Paul Soglin would be an atrocious statewide candidate even though he's popular in Madison.
To answer the question, they should run Kind. He's far and away their best candidate and head-and-shoulders ahead of the other options here.