Hi there!
I live and work just north of Milwaukee (Germantown, WI). Many of my coworkers live in Wauwatosa and speak well of it, its suburban life and its a short drive to University Hill.
Ins
+ Entertainment is cheap. Baseball, hockey, and concerts are considerably cheaper than Chicago.
+ MKE airport is cheap with tons of destinations. I had my pick of the litter of departure and arrival dates to use my United points.
+ Taxes and cost of living are on the inexpensive end for a big city. I keep up on job opportunities outside our area, and many are less appealing due to their higher COL / taxes.
+ Many opportunities to give your time in a nearby community and have a huge positive impact.
+ Lakes and charming little towns are minutes away.
+ Outdoor recreation is aplenty, an outdoorsman (or woman) would be right at home with the hiking trails, hunting, and fishing.
Outs
- Very racially segregated city, so don't expect much of a melting pot.
- Wrong neighborhoods have high crime.
- Booze is a big part of Milwaukee culture. Every festival will have innumerable beer tents. Could be positive or negative depending on your outlook.
- Winters can be cold and windy, while summers can be hot and humid.
All that being said, MKE is high on our list of places to retire once we get to that age. Our biggest concern is the housing cost would require us to work longer (i.e. paying $200k for a house down here vs. $100k up in Oshkosh), which probably isn't a huge deal for someone in your housing price range.
Best of luck!