Having lived in the Sheboygan area all my life i feel i can add some input here.
Sheboygan is slow,just shy of "stopped" if your looking for any real entertainment in any respect,we do have the JMK art center,a theater group,
(up-scale as joe-blow off the street wouldnt attend),and a few other`s .
Change is slow here,with petty rifts in government that hinders the effectivness of the local government as a whole (all departments).
The Kohler area (5 miles west of sheboygan) is "snooty",,i lived there 2 years,if you dont have money you will not "fit-in" (no offense meant to those who live there but it is an honest observation).
Sheboygan Falls (7 miles west of sheboygan,borders Kohler) is a FANTASTIC area ,great people,small town living,great schools and those who live there tend to "keep it real".(i lived there 6 years)
One thing that should be pointed out is you can drive to either Green bay or milwaukee in less than an hour for any pick of entertainment,this is part of what makes the Sheboygan are unique,you can have the small town life well within a short driving distance to big city amenities.
Tax`s are high,jobs are scarce,good restaurants are here but you need to hunt them down,Sheboygan is what you yourself wish to make of it should you choose to make the move,i do disagree with the "outsider" type comments,people are welcomed here from all over the world every day.
Nieghborhoods within the city itself can be "tight" where others in the central city could care less and the subdivisions you most likely will be loved or hated by your immediate neighbors (those on either side of you) with no in-between.
I added a couple of links,hope they help.
http://www.sheboyganfalls.org/
http://www.sheboygan.org/
http://www.destinationkohler.com/
http://www.weillcenter.com/