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I am not sure if this is a warranted feeling, but I feel like using "would" twice sounds kind of ungrammatical. Also, I looked at the n-gram for this and I barely get any result.

Here's the sentence I was trying to write:

If you were the President, would the first thing you would do be trying to enact Medicare for all?

Like I said, I feel it's weird to have two would, would you replace the second would with something else?

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It's not a beautiful sentence but there's nothing ungrammatical or confusing about it.

You could contract the second "would" to ease the problem slightly:

If you were the President, would the first thing you'd do be trying to enact Medicare for all?

Or perhaps

If you were the President, would the first thing you'd try to do be Medicare for all?

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