Are you looking for immediately north of Milwaukee or a bit further. Any of the north shore communities are nice. Whitefish Bay, Mequon, Port Washington.
I have a few friends that are teachers and finding jobs outside of MPS was difficult. Not sure about special ed though. I have always thought there was a pretty big demand for that specialty, but I am not a teacher. Sorry, not really helpful.
Daycare really varies on where you are living. I have friends that pay $200 a week out further in the country and then some that pay closer to $300 a week closer to the metro Milwaukee area. These are for centers. It is much cheaper for in home.