Thought I posted this already, but can't seem to find it after my Thanksgiving hiatus...
With our flight arriving at 5:45 we were hoping to have an ADR that evening, but what are your thoughts...should we take that chance? What is the earliest you would schedule the ADR with this arrival time? AND...is Disney at all lenient with last minute cancellations should our flight be delayed?
Personally, with that time frame, I wouldn't book an ADR. We arrive around 530ish, and with winter weather, you just never know about delays. Even if your own flights are unaffected by weather, other flights can be, causing your flight to be backed up on the runway or having to wait longer to land based on the amount of flights in front of you.
Even if you land right on time, factoring in getting off the plane, bathroom stops, getting to ME, potential wait times for ME, and travel time...the soonest I would make an ADR would be about 8 or 8:30pm, and it would be somewhere at my resort or one close by. Maybe Disney Springs depending on resort, or if you took Uber or your own car (which would then take waiting for Magical Express out of the time table, but also add in the wait for the rental car).
I would sit down and calculate all of the things you have to do once you get off the plane, and see how it feels to you. See if it seems like it will be hectic and you'll be stressed by rushing around, or if you think you'll be fueled by excitement and the desire to go,go,go. The soonest we've ever made it to our resort was an hour after landing, but that was when everything worked perfectly - the ME bus was full and drove away right after we boarded. Otherwise, we've had a 15 minute or so wait for other arriving passengers.
You would also have to be ok with giving up the no show fee if they didn't allow you to cancel. Even though Disney is very accommodating, it's no guarantee that they'll waive the fee on arrival day, when guests know there is potential for plans to go awry.
Good luck making your decision!! I've been in the same position!