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Truthfully, at least in my limited experience with private schools, they can keep his records until the bills are paid.
The thing is though, I would go ahead and pay on the 16th like you've said. It really shouldn't effect ANYTHING as long as his new school gets his records before the next year begins. Also, public school may be a better option for you if you are unable to pay for all of the things required for private education. At public schools, you can at least know that you would be able to get free/reduced lunch, which should help you substantially.
Good luck.
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"School is shortened, discipline relaxed, philosophies, histories, languages dropped, English and spelling gradually gradually neglected, finally almost completely ignored. Life is immediate, the job counts, pleasure lies all about after work. Why learn anything save pressing buttons, pulling switches, fitting nuts and bolts?" Bradbury, Ray Fahrenheit 451 p 55-56
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