Once you leave the airport, you're going to find the airlines a bit difficult to work with! It 'used to be', that DME asked how many bags you had tagged. That way, if the correct number didn't come through, they went in search of it. And this is why we told people that if you don't ride the bus, they won't know how many bags to look for. However...they no longer seem to ask how many bags to look for, so all bets are off.
If you arrive at, say, 2pm, and get to your resort by 3:30, you can 'assume' your bags will be in your room by 7:30. That's what Disney tells us to expect...bags in the room 3-4 hrs after resort arrival. BUT...if you go off to a park for the evening, and return at, say, 11pm, and you find that only half of your bags are there? You've now got almost 9 hours since your bags left the airport....the airlines aren't going to be happy tracking them.
I've had a bag not get to my room for almost 8 hrs after resort arrival. BUT....I changed resorts about 45 days prior to arrival....it should have been fine, but the bag went to the old resort and sat there. No one thought anything of it!!! It took 3 hrs to figure out what had happened to it!!! Waiting until 1:30am is not the way you want to start your vacation!!