Good question and other opinions, of course are welcome. Side note, I am rehabbing my first Court too!
My bags generally improve with 2-3 apps of Leather Therapy RC/ Leather CPR. This is my thinking only, perhaps they chose a stiffer leather for the Court because it has a more structured shape. Also, the flap is lined, the back and under the flap is reinforced with slip pockets so while the leather is supple on my Court after CPR and Obenauf’s Oil (it was super dry) it is not squishy like my red Pocket Bag that lived it's life on a shelf and does not have a lines flap! It’s boxy shape is reinforced by the lined flap and slip pockets.
I have also come to accept that for reasons unknown to me, the leather rehabs differently on some bags. I have had a few meh rehabs, a lot of good to great outcomes and a few a-may-zing outcomes.