We always take the earliest flight out of Midway. The plane sits on the ground at the gate overnight, so it always, or almost always, takes off on time. And then we get to Disney early. But the wake up at 2:30am is a little tough.
You wouldn't think it would have been crowded on a Wednesday morning. We often arrive on Wednesday mornings and it is usually quiet at the DME check in. There must have been a lot of runners who all decided to get there early.
Your villa looks really nice. I would think that the kitchen would come in really handy. I would love to stay at BLT if they ever have a big discount for them. The view and the location would be amazing. I wouldn't mind a Bay Lake view. It would be relaxing.