Disney's Magical Express is free to any Disney resort guest. Flying into the Orlando Airport and staying at WDW resort -- such as Fort Wilderness -- entitles a guest to this service.
I would suggest that he (or you) go ahead and makes a reservation for him for the day and flight he may be taking. That way a spot is reserved for him on one of the Magical Express buses. If the reservation is made far enough in advance, he may also be able to receive the Magical Express luggage tags which he would place on his checked luggage at his home airport and then when he arrives in Orlando, he would just have to check in at the Magical Express desk where he will be directed to a line to wait for the next scheduled bus to take him to Fort Wilderness. If he doesn't receive the tags in time, no problem, he can describe his luggage to the Cast Member at the Magical Express desk and they will have someone bring his luggage to Fort Wilderness. He can, of course, always pick up his own luggage from the luggage carousel and take it with him to the Magical Express check-in desk and then it will be placed under the bus and brought with him to Fort Wilderness.
Resort Guests should contact Disney's Magical Express Guest Services at 866-599-0951. And they should be able to answer all your questions.
Here is a link from Allearsnet.com which explains, in great detail, all about Disney's Magical Express --
http://allears.net/acc/mexpress.htm
If for some reason, he is unable to join you, no worries. You (or he) can call and cancel his reservation. And if a cancellation is not made, don't stress over it. They won't charge you for a "no show."
Hope this helps and it definitely should save you a ton of money over a cab fare.
