Figures that the post that finally makes me de-lurk isn't really about finances!
I was born and raised in Rhinelander (spent a few years living in Madison, then left the state), and I NEVER thought I'd see the day that someone would consider choosing between my hometown and Paris LOL!
Here are things to consider, if you are looking to retire in WI.
Overall, it is a beautiful state, especially if your primary focus is the outdoors/hunting/fishing. Topography and climate vary a lot. The southern half the state tends to be hardwood forest interspersed with rolling agricultural fields, and more topography, fewer lakes, but still a lot of water. The northern half tends to be more mixed hardwood/pine, economies based on logging, mining, and tourism, with tons of lakes and swamps/wetlands (and more mosquitoes), and sandier soil.
Four distinct seasons in the south, not much of a spring in the northern half...Rhinelander tends to go from freezing, gloomy, rainy/mud straight to glorious summer in about 2 weeks in late May. Springs in Madison start about now, but tend to be wet and chilly for the next month. Summer, and especially autumn, are fantastic all over the state.
Winters are cold and long, especially in the north, though less so than when I was growing up (Rhinelander has warmed up by one climate zone since I was a kid). Honestly, though, what was hardest for me was how short and gloomy the winter days are, again, worse up north). This is less of a problem if you are retired, though, because you can dash outside to take advantage of any speck of sun! But if you are light sensitive, this is definitely something to consider.
Growing season is very short in the north. We had a decent garden in Rhinelander, but it required a ton of soil amendment with horse and chicken manure. Growing season in Madison area was about 2 months longer. Also, you will need to fence off the deer, rabbits, etc.
Topography is rolling and/or bluffy in the south and west along the river, and generally flatter in the north and east. Soil is richer in the southern half, and sandier/more sterile in the norther half.
Politics tend to be mixed, with Madison being much more liberal than the rest of the state. The small towns tend to be very conservative.
Economically, Madison tends to be very diverse and robust, with low unemployment. Cost of living is fairly high there compared with the rest of the state. Economically, the rest of the state is doing only variably well. Rhinelander (I understand) is currently in a tough spot because one of its foundation businesses, the paper mill, is on the bubble of potentially shutting down. Rhinelander does have an airport and a decent hospital, which gives it a bit of a leg up as far as the northern touristy communities.
Generally, WI is considered a fairly high tax state and not especially great for retirees, esp in regard to property taxes, though this might be offset by sheltered military retirement income. However, one thing the high taxes have traditionally bought is a fairly robust safety net for aging seniors. For example, we had considered moving my aging mother back to WI (out of TX where we currently live, and which has much less support for aging seniors). However, the current politics of WI have swung strongly to cutting taxes and services, so this could change in the future. If you are independent financially, this might not be a consideration anyway.
Except in the bigger towns and cities, the culture is mostly focused on hunting, fishing, football, bars, small homesteading, boating, and winter sports. If you want an arts/music/theater/literature scene, you will want to be in Madison or Milwaukee, or maybe one of the smaller college towns like Eau Claire or Stevens Point, or Spring Green (a favorite of mine), which is partly based around an outstanding classical theater company (APT). Rhinelander does have a good community college with a little bit of associated arts, but again, it is a very small community so culture opps are limited.
My personal experience was that I absolutely LOVED growing up in Rhinelander, doing the small homestead thing, living on lakefront property, running nekkid through the woods as a little kid. And the LAKES! SO MUCH WATER! I was miserable leaving it when we moved when I was a teenager. But we moved to Madison, and I soon discovered that overall I liked the southern half of the state more because of the better climate and the lovely topography. Eventually, I moved out of state to go to college, and now I would only consider moving back to WI to particular locations and under very particular conditions. Rhinelander would NOT be on my list, and I say that as a member of one of the 'founding' backbone families of that town. For me, personally, it's too dark, cold, conservative, economically limited, and parochial. I sure love to visit it in the summer and autumn though!
In contrast, I would most certainly consider living in Madison (and I visit there much more often), or anywhere in the SW quarter of the state, as long as I took steps to deal with my seasonal affective disorder. SO BEAUTIFUL, SO GREEN, plus quite a lot to do!
Feel free to ask questions.