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Milwaukee for the lake, and it’s genuinely a great town all around. Culture and location overrides any shortcomings for me.
The Twin Cities are great, and the supposed isolation would never be a problem for me since I’ve never lived in a major metro where I got so bored I felt I had to go to another nearby one for a good time. It wins some of the criteria, for sure.
I still like Milwaukee better as a place to live based purely on personal preference.
Throwing Madison in with Milwaukee adds no appeal outside of economic interests, but for this unusual comparison, it does little else for Milwaukee as a place to live. As has been previously mentioned, the average person in Milwaukee isn’t likely to head over to Madison very often because there’s no reason to. Far, far more do seem to go to Chicagoland somewhat regularly.
It's hard to compare Minneapolis/St. Paul (which are part of one large metro area) to Milwaukee/Madison (which are not very near), so I will just compare the Twin Cities with Milwaukee. Overall, the Twin Cities win this in almost every area. Milwaukee is a great city, but its proximity to Chicago is, in a sense, its downfall because Chicago sort of leaves Milwaukee behind as a third tier city. In the opposite way, the Twin Cities is sort of unique because it is sort of a hothouse of its own culture, economy and other sectors. Also, the Twin Cities have a much more dynamic, urban feeling. This is just the impression that I had.
Quality of life: Minneapolis/St. Paul
Things to do: Minneapolis/St. Paul
Transportation: Minneapolis/St. Paul
Economy: Minneapolis/St. Paul
Recreation: Minneapolis/St. Paul
Education: Minneapolis/St. Paul
Sports: Minneapolis/St. Paul
Night Life: Minneapolis/St. Paul
While Milwaukee's population (590,000) is larger than either Minneapolls or St. Paul individually, the Twin Cities together are significantly larger (730,000). On top of that, Milwaukee's CSA metro population is just above 2 million whereas the Minneapolis/St. Paul CSA metro population is 4 million. So they are really in different categories.
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