It's been 2 weeks and I'm posting a followup to this thread. Since then, we've booked our flights on Southwest, but the arrival flight that we'd like in the morning is still too pricey, and so we've booked a flight the night before, arriving at MCO about 11pm. If the morning flight comes down in price I'll swap reservations and pay the difference. But if it doesn't we'll probably book a hotel room and take the DME about 7-8am in the morning as we've done before.
Or maybe not. Thanks to the info in this thread, we're seriously contemplating hanging at MCO for a short while, then taking the DME at 12:01 to our resort (arriving about 1am) and having them hold the bags there. This gives us about 5 hours until we can formally check in at 6am and then eat at the Club Lounge at 7am. I called the Signature Services line and they confirmed we can indeed do this.
But why? The way we see it, by taking the morning flight, we have to leave our house at 3am to get to the airport. Our teenage daughters usually pull an "all nighter" when we do this. By arriving the night before, they'll just be pulling the "all nighter" in the lobby/club lounge (no food served) of a resort hotel. We're going to try it this time and see how it goes.
Thoughts anyone?