I love it; we have a situation that's almost the same.
Mits, my boy, at 11:00pm exactly will come by my chair and insist that I go up stairs to bed. If I am not fast enough in 5 minuets he will be back. When he gets me tucked in he will wait at the foot of the bed for my wife to join us. The he will tuck in under my arm and purr. As soon as he is sure we are going to sleep, 10-15 minutes, he will make the rounds of the house. Checking on the other 9 and making sure the food bowls and water are properly filled. Mits then will join us again, usually on my wife’s pillow and go to sleep for the night. God forbid that I get up during the night, as he has to go though the whole routine again.