A simple cost of living indicator shows that someone earning $100k in Milwaukee would need to earn $160k in White Plains to maintain the standard of living.
That said.... nobody lives in White Plains. White Plains is a huge office park criss-crossed by very busy and (usually) congested highways. Yes it's in the suburbs but Westchester is densely populated. Nearly everyone who works in White Plains lives somewhere else; if they earn enough then they stay in Westchester although the taxes are much higher than they are just over the border in Connecticut. Some live across the Tap which spans the Hudson (the Tappan Zee bridge) but that's a parking lot for 6 hours a day; the trade-off is that living in Orange or Rockland counties is much cheaper than Westchester so people do it. Some people live further upstate, in Putnam or Dutchess counties. These areas are also cheaper, in comparison, but still not as cheap as across the river. The attraction to staying on the Westchester-side of the river is that you have train service to Westchester from Putnam and Dutchess but none from the Orange/Rockland side (you
must to drive).
If you move be prepared for spending time in traffic. Westchester contains the major arteries to NYC from upstate New York and New England. There are interstate spurs, bypasses, bridges, tolls, and lots of parkway-style roads from 70 years ago not meant for the volume or speed of modern traffic. In short, the driving is horrendous. I HIGHLY suggest coming to visit and drive around to see what I'm talking about. Also consider New York is the most highly-taxed state in the country (finally surpassing Taxachusetts last year) both in sales, income, and property taxes. Think over this move very, very, carefully and know your COL differentials to be sure you're not going to end-up earning less in real terms.
The good parts are that Westchester usually has the best schools in the state, generally very nice towns, and quick access to NYC (the best city in the world
).
Good luck Scott!