I'd say around 9
You have to get from the plane to your resort, remembering that because the plane lands at 5:18 doesn't mean that's when it gets to the gate; let's say you get off at 5:30. Ten minutes to DME, twenty minutes to check in and board your bus, 45 minutes to your resort (bus will probably stop at one or more other resorts first), ten minutes to check in, twenty minutes to get to your room and freshen up. Okay, now it's 7:15. Thirty minutes to get from your room to the bus stop and then on to a switching location since no bus goes from resort to resort. Say you choose MGM. Then twenty minutes for the boat or bus to Yacht Club. It's recommended you arrive five to ten minutes early.
Since all times above are ideal, that is, your transportation is ready to go when you arrive at the waiting area and goes directly to your switching location, build in an extra half hour for when this doesn't happen. Voila! 9 PM!
Of course, you can save a great deal of time by taking a cab from POFQ to YC.