As a longtime recovering Chicagoan (moved away almost 40 years ago), the only thing I'd argue in the evaluations here of the Clare is that because it's in the North Michigan Avenue/Gold Coast area, crime probably isn't a big deal. It's one of the wealthiest areas of the city and probably one of the safest. Of course, if you venture to many areas of the South Side -- or even worse, west a few miles from the Loop and past the United Center -- it's a much different story.
Interestingly, there's sort of a "mini-Villages" (a Del Webb community) about 50 miles northwest of Chicago near Huntley, Ill. I think it's been there 25 years or so and has a population of around 10,000. But no matter how nice it might be, it can't escape Illinois' drawbacks -- weather and taxes (and you'd better enjoy a view of cornfields).
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