Bah.
What is it, 20F for the winter? Days are longer than they are here and snowfall doesn't look too bad. I've hunted in worse. First time I went after Hinds in Scotland I was there a week and it never got above 15F the whole time. Never stopped blowing a gale either. I was still out on the hill every day from dawn till dusk. It's character building!
I think Texas is making you soft Red Leg!
I'm not saying you haven't done your research, but according to the page weather-atlas.com, we see:
"Winters are cold, snowy, and temperatures around -30°F (-34.4°C) are common in the northern counties - in fact, during the coldest month of January the mercury may plummet to -40°F (-40°C). Clouds cover the skies for a significant part of the year in many places. The north, west, and central Wisconsin regions have a short growing season on account of a small freeze-free period compared to the eastern and southern regions that have the warm impact of Lake Michigan."
So you may have dropped a negative sign there. But then again, unlike Scotland, it's a dry cold.
In any case, yes there are some differences. Because more people hunt, management is approached from a different point of view. Unlike, say, Roe in Germany where it's "keep going until we tell you to stop or you get bored", you tend to be limited to a given quantity (hence the tags). The zones are also because the requirements in a given area of the state vary, but the licensing is for the entire state, so it's a convenient way to separate the requirements. And the yearly plan for the number of animals harvested is what will drive tag lotteries for specific species. There are not a lot of bear in Wisconsin, so they only want to take few in a given year. Hence, the lottery will "balance out" who gets the chance to hunt, and the preference points come to play the longer you are trying.
There are other states with bear that are not so limited in opportunities. The more remote, the more likely you are to find guided hunts. For example, fancy a grizzly in Alaska? Easy but expensive. In the lower 48 it's all black bear, and there are places where you really need to know the difference, and the difference is NOT color.
I'll leave it up to you to sort our the firearms piece, but it sounds like you have a handle on that. So go to your safety course and get your hunting license. You will find the process ludicrously simple compared to anywhere in Europe. Joint the hunting/shooting club, and you'll meet like minded souls who will help you. I'm not sure what is near Milwaukee, but rural land is not that far away. The state licensing agency will be able to tell you if there is public land where hunting is welcome for all.
Oh, and one more thing that we've been dancing around because we are so used to it, but is a bit different than the UK: Your license will be for the state of Wisconsin. You can take your firearm anywhere to hunt (and I encourage this!) but you'll need to buy a non-resident license for other states. This is not difficult (but can be considered expensive, in comparison to a resident license), but it's an important point. The way I explain it to my German friends is they don't expect their German license to be good by itself in Austria or Slovakia, so why should Wisconsin be any different? "But it's one country!" they exclaim. Yes, a sovereign country made up of fifty sovereign states. Welcome to federalism. It's a feature, not a bug.
Waidmannsheil!