A $15 taxi gets you downtown (15-20 drive, 40 min bus ride). So you are near a great nightlife and lots of restaurants. Everything in Milwaukee County has crazy property taxes ($25-$30 per 1k) which stinks, but at least you get low crime and top schools for your buck. Shorewood has more apartments and duplexes than Whitefish Bay, it's a bit more transient (e.g. more renters, lower average years of property ownership), a bit more liberal, a bit younger, and a bit more diverse than Whitefish Bay- otherwise they are pretty similar. Glendale is a cheaper alternative to Shorewood (but not as nice). If you like Shorewood but can't make the reach financially, check out Wauwatosa, Glendale, Bay View and Riverwest (probably in that order). If you have kids, stay out of MPS school district. Shorewood and Whitefish bay are top notch. If you're willing to be a bit further from Downtown, Brookfield has very good schools also. I live in Shorewood so I say it should be your top pick.