NOTE: I'm only here to answer this question, nothing else. No implications.What major problem is this rule designed to fix?
5 days before the deadline, Harold had to call 27 teams about payments that were yet to be made. There are only 53 teams at states; 51% of teams had not PAID yet for the state tournament 5 days before the deadline. Maybe high schoolers don't understand how ridiculous and disrupting this is to the organization of a tournament of New York's size, and it's certainly no one's fault, as I myself would not have realized only a year ago. Necessary payments and logistics simply cannot be made and done when over half of the money has not been submitted. Every SO organization runs on very limited budgets (so close to breaking even and making losses that it's impossible to describe without a financial statement in hand), so every payment counts and needs to be paid for things to be booked, bought, and planned.
There is a serious urgency to be had when so much money has not been paid, which would also explain Harold's unwillingness to contact multiple coaches from a school; that's not his job, and he almost definitely does not have the time. It's easy for everyone to clamor on why he couldn't just spend "the extra five minutes on email," but again, no one who has not coordinated a gigantic thing like this has any right to be so critical of positions they have not been in themselves.
This is the reason for the deadlines. This is the reason such rules are in place. No one who has not planned a huge tournament and managed finances as such can know exactly how much pigeon needs to be shuffled around for everything to fall in place in time. Organizing NYSSO is no small feat.
Just a perspective to chew on for those students who wonder why directors like Harold make such a big fuss over payment deadlines. There are serious constraints one needs to consider, and again, it's no fault of the students that they're missing the perspective. I hope this makes the situation a bit more clear.