We done this a number of times. It has always worked well for us. In fact, I've decided I like it better than flying in the morning.
First of all, depending on your schedule, going the night before will give you a few hours for final trip preps. When I fly in the a.m. - there are always last minute preps - like packing my hairbrush and makeup - that just can't be done ahead of time. That makes for a hectic morning for me. Even if you have to work on Thursday, you'll still probably get a little prep time that day.
In 2005, we saved a LOT of money by flying in on Thursday night. We didn't arrive until nearly midnight, and it took a little while to get our car, room, bags. Remember, it will take you a while just to get out of the airport and to the hotel. If your flight is delayed (weather?), they usually won't cancel it -because they need the plane to be in Orlando for the a.m. schedule. On that trip, we stayed at a cheap I-Drive place for the first night. It was great!
When we finally got to our room that night we were all hungry (you eat dinner early, but all that going burns calories), so we went to the Denny's on I-Drive for carry out. They serve breakfast food 24hrs. a day, which is exactly what we wanted.
The Disney eateries often close by midnight, so after that on Disney, you might be out of luck (in that case we ate the last of our crummy airline crackers, and got up early for breakfast). The Swan/Dolphin have late night options,and I think the Deluxe resorts have more late night options. In any event, I'd plan on having SOME sort of snack ready upon your arrival.
The best part of flying late was waking up in Orlando the next morning! Since the extra time wasn't part of the original intinerary, we didn't plan it as a full park day. Just being in Orlando was WONDERFUL and a joy unto itself. We had a nice swim in the pool after breakfast, and went to DTD later that day,as we had orginally planned. (When we flew in the morning, the opposite happened. We planned it as a park day. None of us slept much the night before, and we were so tired by the time we got our room and had lunch, that we just wanted to nap. Instead of losing the day on our tickets, we ended up going to the parks for two hours before dinner. It was kind of a waste.)
On another trip, we had a late afternoon flight, so it was an early evening arrival. In that case, we stocked up on a few groceries and headed to DTD for a little while.
Night arrivals can also be perfect for touring your resort, and getting in a little hot tub/pool dip before bed.
