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Manitowoc would be similar to Sheboygan in that you can find things on your list in the downtown area (library, etc.) but the grocery stores are out by the expressway.
Manitowoc has a nice "Y", very popular, also has daycare, I've seen the kids playing outside in a large outside enclosed area. It is right by the lake, the walking path goes right by it. Parks are nice, well kept, clean, there is even a small zoo, I walk there frequently.
I live in Two Rivers, which is next to Manitowoc and small, 12,000+ people. I'm retired so it works for me as I wanted a walkable town, I'm close to a grocery store and "up town" is only a 1 mile walk. Two Rivers is tricky weather wise as it is on a little bump out and it varies from Manitowoc as much as 15 to 20 degrees (not an exageration)!
You can private message me if you have any direct questions, both Manitowoc and Sheboygan have websites and you can get info mailed to you. I moved from Illinois to Wisconsin Fall 2007 and I received a helpful book from Manitowoc. In fact, they mail it to all residents every year, its called questions and answers I think.
Good luck!
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