Need 13 stays to retain Hilton gold by EOY. Is it worth switching properties every night for a month?

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Nope. As a Hilton diamond member, I find the program blows. I also have status on other programs so maybe I don't care, not sure if OP does.

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Yup. AMEX Platinum, at least the personal card, comes with Hilton Gold and SPG Gold.

While not having status at hotels is far less burdensome than lacking airline status, it’s still good to have it at the majority of properties, even lower tiers.

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Just get the Hilton Surpass Amex Card and spend $1000

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Just get AmEx Platinum card, especially if DL is your airline

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Deloitte has a status challenge up for Hilton, you should be able to get it with 4 stays

I would do it.

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