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?