Yes, you can pay for classes of that year and/or classes that start the first three months of the following year.
You can pay in December for classes that start in January (or February or March).
The last year, you might want to pay the following year (in January) in order to have expenses for a credit that year, but it depends on how much expenses are paid each year.
Box 4 can be all sorts of adjustments, such as dropping a class. You would need to ask the school what it is for. TurboTax does not do anything with Box 4 since it does not know what the school put in there.
Remember that a 529 distribution can be allocated to Room and Board. Room and Board makes a distribution non-taxed but not so when allocated to a scholarship.
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