...But my main concerns are relocating (I like it here in Wisconsin) and being surrounded by others who might eat away at my edge if they see what I'm doing. Is it worth the move and the experience?
That right there should be your answer to stay where you're at.
I've once lived in the summer in NY (lived with a college buddy) and WI (Madeline Island with a relative) although never spent any time in Milwaukee WI...
Cost of living and quality of life is a big issue for me. I'm not a big fan of Milwaukee but NYC I could never reside in reference to the city itself.
The issue is that you're asking the opinions of anonymous people that know nothing about your lifestyle/costs in Milwaukee in comparison to your lifestyle/costs in New York
City (assuming you're not talking about some suburb in the state of New York). Also, you mention nothing about your family/relationships.
Without the info about family/relationships, Milwaukee has the edge and I think a trial run in NYC for a summer would be enough for you to make a better decision. Thus, a full year not needed. Yet, make sure you make arrangements in Milwaukee just in case you decide to return. For example, if you own your house/condo...sublease it for 1 year or rent it for one year.
If you're renting, you can make arrangements with your landlord to only sublet it on a one year term.
What's your cost of living in Milwaukee per year ?
What will be your cost of living in New York City per year ?
wrbtrader