Sheboygan is located on Lake Michigan, which is a great feature. The lake is scenic, provides recreation, and moderates the climate by keeping it cooler in summer and "warmer" in winter. Seasons are about 2 weeks behind because of the lake. Winters are cold from December through February, but not many days are brutally cold. Summers are hot from June through September, but not many days are brutally hot. Spring and Autumn are my favorite, though if you like hot weather, you will find them too cool for your taste. The vast majority of days have pleasant weather, and the skies are clear more often then not.
There are nice parks and nature areas in and around the city. Shopping consists of standard stores, mostly at malls, but we do have some unique shops in the downtown area. We are actually a bit limited in franchise restaurants compared to some cities, which is fine with me. We do, however, have some fantastic restaurants, unique to our city. The city infrastructure is good, and you will not feel crowded anywhere. For more sophisticated tastes, shopping options, and night life, Kohler (3 minutes away) will help you spend loads of money on high class merchandise, Milwaukee and Green Bay are each 1 hour away, and Madison 2 hours away, and Chicago 2.5 hours away. Those are also your choices for airports.
We have some nice golf courses, including Blackwolf Run and Whistling Straits of Kohler fame. Popular recreation includes charter fishing, boating, jet-skiing, sailing, wind-surfing, kite-surfing, surfing, swimming, fishing, biking, disc golf, golf, auto racing, and team sports.
Night life consists of bars, restaurants, a limited amount of musical venues, a stage theatre featuring classical music and some big acts, and a cinema. As for the bars, only a few can be considered upscale, and they are primarily attached to the upscale restaurants. The vast majority of bars are family-owned, and tend to have an established group of patrons. You can eventually find an atmosphere that suites you. As for night clubs/dance clubs, Sheboygan has a hard time sustaining night clubs. They will typically survive for only a matter of months. There are several places to get great beer and/or fine wine. Again, Kohler has something to offer in this department.
Restaurants range from cheap to high class with a good selection of American, Italian, Asian / Hmong / Thai, trendy food, health food, and fast food.
I'm not qualified to comment on the public schools, though I know they have a good reputation.
Politics are conservative, religion is popular, common sense is about as common as anywhere else, and higher education is optional. We have a transit system, but most of the time the buses drive around empty. They are nice buses though. Taxi cabs are available, but you will need to call the cab company for a ride. They don't cruise the streets, except for major events and things like Haloween night.
We don't have bike lanes, which means you'll want to avoid biking on the major streets. You can easily find a side street to get you to your destination safely. The drivers in Sheboygan seem to forget the same traffic laws apply to bicyclists and seem to do all sorts of strange variations on traffic law when a biker is present. Drivers here are not as used to seeing bicyclists as those in larger cities.