Q1: Can the payment I made in December 2023 for spring semester 2024 be added to the total of box 1 from both 1098-T to raise the qualified expenses in 2024?
A. No. The payment must be made in the tax year to count on that year's taxes. That payment counts on your 2023 tax return.
Q2: What kind of scholarship can be considered a hybrid between earned and unearned income?
A. Any scholarship that is, in deed, a scholarship. The school posting it to box 5 of the 1098-T is one indication, but not a "proof positive". Out of the $7575 in box 5, $6000 was paid directly to the school from a non profit organization.
Q. Can some of this scholarship be treated as earned income to get the $14600 standard deduction?
A. You are going to have to make that determination. On the little info provided, the $6000 form a non profit sounds like a scholarship. The $2000 prize from a private firm, not so much.