I would have been so mad if they didn't pick up until 5:30. I get upset when parents are 5 minutes late! I would also enforce a late fee. Mine is $1 per minute as well. I had a dad who was late a few times. I talked to the mom about it and it quickly stopped. My daughter has activities that we have to get too during the week and my families know I am in a hurry to go. I would never ever extend my pickup time for one family. I used to be closed at 5:15 and had 1 family who picked up then. Those last 15 minutes felt like forever!! When the left I quickly changed my closing time and never looked back.