$2500 is far more than most people in Milwaukee pay for housing, this isn't Seattle, San Francisco or New York, after all. Your budget is absurdly high, I would recommend touring the water street area, a large number of new condominiums will be there, that area should meet your needs well. With that budget, I would assume that you plan on living downtown. Areas like Bayview, Walwuatosa, as well as Shorewood, are also worth exploring. All three have very different feels, some more hip and young, some more refined suburban. It all depends what you're looking for in the city. You won't spend 2500 on a place in those areas unless you're looking at 4 bedroom houses with big yards though.

I live in the same neighborhood as Contour and absolutely love it, nowhere in the city I would rather live. Super easy access to the lake, parks, restaurants, grocery stores and it's just a really friendly, beautiful area. You'll be right across the street from Colectivo, and trust me, you're gonna love it.