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I'm placing odds at 3-1 *against* making the 9PM flight.
You're going to have to be pulling into DCA at 7:30 at the latest in order to turn in your rental, go through security on a Friday night in DC with the million other travelers, congressmen, and tourists leaving the city, and make it to the gate in time to check in before they close the doors 20 minutes before the flight leaves.
Unless you leave at 5PM, I say NO chance you make it.
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