trivial said:
Hmm, so doing the luggage ourselves is an option; good to know.
How long does it usually take from the time you arrive at the airport until you're at your resort? (Trying to make sure my dinner reservations aren't cutting it too close.)
It varies a lot. The bus ride itself takes about 30 minutes. However, it can stop at up to 4 hotels. Our bus only had passengers going to one hotel (Caribbean Beach Resort), which our driver said was the first time it had happened to him.
Give yourself about 20 minutes to de-plane and take the tram to the main terminal, orientate yourself on level 3 and find the Magical Express counter on level 1. It's 5-10 minutes to check in for your bus ride and get in line. There are at least a dozen lines, each going to different Disney resort hotels.
Once you're in line, there's usually a short wait to board the bus and then a short wait before the bus leaves the airport.
The above activities might add up to about an hour before arriving at your hotel.
Once you're at your hotel, you'll probably check in at the registration desk to get your room keys and activate any park passes and dining plan. Then you may or may not go to your room to freshen up. Then after that, you're ready to go to your ADR location.
On the day I went to WDW 2.5 weeks ago, I landed in Orlando at 7:00 p.m. and arrived at my restaurant of choice in Downtown Disney via a Disney bus shortly after 9:00 p.m. My Magical Express bus was a charter to my hotel or it would've taken slightly longer.