I'm usually pretty "stay at Disney" not the airport - but.... in this case......
Two scenarios:
1) Take ME to Disney, stay at value or mod. Wait in line to check in, wait forever for your luggage to show up four hours later. Unpack enough to sleep, pack up the next morning, take bus to PARK with luggage, transfer to bus to new resort with all your luggage, check in again, drop off stuff, off to park. This plan gets alot better if you take a taxi between the two resorts - but that will cost you $20-$30. Values only have double beds - typically too short for a tall guy. Mods have queens, but cost more.
NOW - you can also ask Disney to TRANSFER your luggage. If you are comfortable with that - this gets easier. You could just haul stuff to bell services, catch a bus to a park - and not worry about checking in until after 4pm - when you know your room will be ready and luggage should be at the new resort.
2) Pick up luggage at airport, haul to room at Hyatt. Queen beds. Check in lines typically short. Do nothing. Unpack enough to sleep. Pack up stuff, Haul stuff to ME, ride bus, check in at hotel at Disney. Off to park.
So - depending upon how you "pick" to handle the transfer between the two resorts, I can see a perspective that staying at the airport is easier.
Me - I'm all about getting to Disney property. I'd walk off plane with my backpack, head to ME, check-in, leave the heavey stuff in the backpack in room and I'd head to Downtown Disney or do a resort tour that first night if I didn't have tickets for that day. Get back not too late, roll into bed - only having to pull out the sleep attire and toiletries pack on top in the checked bag that magically arrived while I was out. Next morning, shower, put on the outfit again planned so its on top in the bag, throw toiletries/dirty clothes/nightshirt back in suitcase, (no digging through suitcases for me!) and I'd pay for the taxi between resorts. (I like to know WHERE my bag is, in case I need something - so I don't like luggage transfer. And it takes too long to do the resort-to-resort thing on the bus). Oh - and grocery delivery schedule for arrival at the resort I'm staying longer, not the first place for the one night. But that's me. Now - with a late arrival - says 7pm or later - I would do the same BUT - I wouldn't check my bag for ME. I'd get it at Baggage Claim and haul it to ME myself so I don't have to wait for it. I don't want to risk my bag showing up TOO late and me waiting for it to go to bed.
However, that wait for luggage for ME until late drives some of my family members crazy, and hauling luggage around hotels is a huge hassle for some of them - so the concept of switching gets more burdensome for them. And one of them has to basically unpack every night - and totally repack the morning. And we are all tall people and none of us like sharing a double bed. And one family member isn't that into Disney - so prefers to be off-property more. All those things play into these decisions.....