1. Barring some unseen development, it seems highly likely that two Milwaukeeans will square off in the race for Governor. Very few Governors have been from Milwaukee. The last, I believe, was Julius Heil, elected in 1938. And there were few before then.
2. This seems to me like an unusual matchup of two relatively personable and "cool" (in the McLuhan sense of being less obvious and more detached from the fray) candidates. Folks like Doyle, Loftus, Chvala, Garvey and even the garrulous Thompson were much more combative and tempermentally partisan. Going negative will be a challenge for both these guys.
3. It may be that the winner will have to be perceived as "from Milwaukee" but not "of Milwaukee," i.e., not associated with the more general view of Milwaukee as being a ungovernable and unsafe morass. Both candidates will have something to say on this, but, given what I expect will be the salience of fiscal issues, I suspect that Walker has the early advantage.