Yes. Still looking for jobs and looking hard.
No plane at the moment. Recently sold share in Piper Warrior that I owned. Looking to instruct as a part time gig for now.
Prefer smaller towns with outdoorsy things to do. No kids, so schools and quality of education does not matter to us. Low crime would be nice. Fine being on either side of the state line. IA is fine too
For airports, prefer something where there is an active pilot community and training.
Cool! Now I'm starting to have ideas.
For reference, I grew up in Middleton (west side of Madison) and now I live in the village of Richfield - Population 11,300 spread over nearly 36 square miles (the township incorporated as a village in 2007 to prevent encroachment by cities) for a population density of 314.7 people per square mile. Lots of great parks in the immediate area, Ice Age Trail very close to me, and less than 15 minutes from I-41 and I-94 when I need to get somewhere.
Wisconsin as a whole is great for outdoorsy things. We generally think about going "up north" for such things but the entire state is pretty outdoorsy, the "up north" thing is to escape the FIBs (that's, uh, "Friendly Illinois Brethren"
) that invade our state on the weekends because they lack the outdoor opportunities that we have.
For both jobs and flight instruction, you're probably going to have the best luck in the Madison or Milwaukee areas. Green Bay and really the whole Fox Valley (basically from Fond du Lac up the west side of Lake Winnebago through Appleton and Green Bay) are fairly populated, but more focused on manufacturing, especially paper.
In the Madison area: Job-wise you have both the main University of Wisconsin-Madison campus (44,000 students) and plenty of IT opportunities around that, the state government, and local companies. UW Health, Meriter, and plenty of opportunities in health care as well. Aviation-wise, you have good opportunities for teaching at KMSN (Wisconsin Aviation), Morey Airplane Company or Capital Flight (C29) as well as a great airpark to live on at 6P3 in Waunakee, which is also a really nice little community that avoids most of the city-ish influences of Madison because it's opposite Lake Mendota from downtown. Madison is a fun airport to fly from due to the wide variety of traffic: Lots of corporate and small GA, flight training, airlines, military (F-16s and choppers based here, but lots of transient military traffic as well).
In the Milwaukee area, there's lots more population but it's still a manageable size city - Even though I live in a very low population density area, I can get to downtown Milwaukee in about 30 minutes - 45 if there's a lot of traffic. Higher ed wise, you've got the University of Wisconsin-Milwaukee, the second-largest of the 13 UW campuses with around 27,000 students as well as Marquette Univeristy and several smaller private colleges. Tons of IT and health care opportunities as well.
Aviation-wise, there are several airports in the Milwaukee area but Waukesha KUES (where I'm based) is the third-busiest airport in the state after Milwaukee KMKE and Madison. It's only a class D but has more traffic than Green Bay, our third class C in the state. LOTS of GA activity, both corporate and small piston, and a pretty large and active warbird community with the Wisconsin Wing of the Commemorative Air Force plus quite a few other based warbirds including jets. The main flight training operator here is Spring City Aviation, though the Stein's FBO does training and rentals as well. Spring City also operates out of KMWC and KBUU. Waukesha is only about an hour from Madison, if that.
Happy to answer any additional questions you have about these or other areas. I'm a lifelong "Cheesehead" and there's a lot to love about this state, both outside of aviation and in, lots of airports and of course the World's Greatest Aviation Celebration!
Way more lakes in Wisconsin...
And they're not all next to freeway overpasses like they are in IL.
BTW, one more vote against Rockford: I specifically remember that when the Money Magazine survey ranked Madison as the best place to live in America, Rockford was #500. Dead. Last. Not a great place to be.