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Sounds like you aren't focused on earning points, but big thing with Residence Inn and Town Place Suites is that you earn half as many points as all other properties. Courtyard, Fairfield, and Spring Hill Suites are on the lower end, safe bet is to go for whichever is newest/most recently renovated. JW Marriotts are generally the best (without getting into the Ritz and Edition properties), followed by Renaissance, then generic Marriotts and Autograph. Since Autographs were former independent hotels, quality can vary a lot by property, but they can be quirkier. https://skift.com/2016/09/21/every-one-of-marriotts-30-hotel-brands-explained/
Thanks for the confusing brief and holiday OOO

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There are hundreds of lakes in WI, MI, & IN people have homes.
Various.
Most popular I know for the wealthy would be Lake Geneva or Lake Michigan from the Indiana Dunes through around St Joe’s Michigan.
Some of the smaller lakes are nice, but inconvenient and not really havens for the wealthy.
I said most popular and that the others weren’t really havens. I never said wealthy Chicagoans didn’t vacation elsewhere.
Michael Jordan has an insane mansion in Highland Park. I’d still say that Lake Shore Drive in Gold Coast is more of a haven for the wealthy than Highland Park.