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Update Feb 5 2024: I have determined the old Tip of the Mitt is now part of Sunrise Beach Motel which is still operating as of 2024. The angle in which the bridge is visible and the distinctive notch at the front of the building sealed the deal.
Thanks to an ad for Cocker Spaniel puppies, I know this motel goes back to at least 1949. I don't have much further on it other than it was on US-27 near US-23, a place where numerous motels sat and still sit today. I don't think this one is still standing but I could be wrong.
I was able to determine the motel was once operated by Frederick E Berakovich. He owned Bell's Melody Motel, the Beachcomber Motel, the Tip of the Mitt Motel, the Dinner Bell, the Peppermint House and the Sail Inn Bar - all in Mackinaw City. He passed away in Feb of 2011. It was also owned by George Rogers at one point as well as Michael and Minnie Estok according to the postcard below.
From Barbara Wort: My uncle George Rogers was the owner of this motel. Wonderful to see the ad about the red cockers as I was given one of the pups in the ‘50s. Awesome to see post cards. They would go to Florida in the winter.