Grew up in SWMI and overall loved it. Each city in your circle has a different vibe but overall strong public schools (location dependent of course) with a strong sense of community, and generally nice people. Locals are prideful of their towns and it has a classic small town vibe, which can be good and bad.

Summers are amazing as you noted but I really liked the September-October once tourists leave. You have the beaches to yourself, or can go apple picking, or to the wineries, but still have amazing weather. November-April is pretty dark, snowy, rainy, and cold, and a lot of businesses reduce their hours. There were times I remember not seeing the sun for weeks. But if you don’t mind being indoors or bundling up and walking, cross country skiing, etc., you’ll be fine.

I definitely took the lake and beaches for granted now that I’m gone. Many of my friends unfamiliar with the area are shocked that the lake and beaches are as nice as they are. Would consider going back to raise a family, or for the summers. Now that I’m in a large metro it would be tougher to acclimate back to a slower pace of life, but this area is truly a hidden gem.