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Switching hotels mid-trip--would you do it?

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DD (24) and I are beginning our plans to visit New York in mid-May, probably for six nights. We are planning to see shows, sightsee, shop...the usual. Between the two of us, plus DH (who is not going) we could likely cobble together free stays for several of the nights using points from Hilton, Marriott, etc. But this would require switching hotels mid-trip, of course, probably several times. Would you do this? Or is it too big of a hassle? Just looking for opinions. Thanks!

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