We used to be fans of the early flights. We would always just work the price of the airport hotel into our
budget. It was expensive though (we usually leave mid-week so we would get hit with business travel prices, usually $300 at the Westin at DTW) and we still had to wake up fairly early. I am a stickler for getting to bag drop at least 90 min before my flight, if not earlier. So with all that considered, we were still waking up at 5:00 am, which I do a few times a week, but it's always brutal, AND we spend all that money. Not ideal. The past couple trips we have been taking a late afternoon/early evening flight out and staying at an offsite property the night before wee check in.
Getting there a bit earlier has made such a difference! This past trip was awesome, we arrived around 6:00 pm. We always rent a car, so we drove to HS and got out APs and bought our TIW card, then we headed to OKW and had dinner at Olivia's before heading to our offsite resort. The next day we woke up without an alarm (luxury) got ready at a leisurely pace (luxury) and left the offsite property around 9:00 am. We drove straight to Publix, got our groceries, and we're checked in by 10:30! Our room was ready, so we dropped our stuff, and we were in Epcot by 11:00 for lunch at F&W!
We didn't plan on this, we actually planned to fly out at 7:05 am. The airline changed our flight time (by like 10 min) so they allows us to change our tickets, and my DH had some meetings get canceled, so the stars sort of aligned for us. It was just wonderful though. Moving forward, this is our plan!