To answer you....yes, I sometimes feel guilty when I charge my late fee. I have only had to charge it 3x and it was to the same family all 3x! I still charged it though because like the others said, we have to enforce our rules and policies because if we let it slide just once, they will assume it's no big deal and will break that rule/policy again. All 3x they didn't text me to let me know they were going to be late so I think it made a bit easier to accept the money though!