Let's go back to the beginning. I just noticed that the decision tree document you posted appears to come from your employer. At the top it says:
"RTX is required by law to withhold Federal, state and unemployment taxes on eligible RTX ESP expenses. Taxes are withheld through payroll deductions".
Note, they further say "taxes will be payroll deducted once the $5250 is surpassed". If that is what happened, you paid tax on $2750 (8000 - 5250 = 2750), then the answer is different. You get to claim the $2750 to calculate the Lifetime Learning Credit (LLC) on your tax return . That's worth an (up to) $550 credit.
Do enter the 1098-T on your tax return. After entering the 1098-T, the TurboTax (TT) interview will eventually ask about employer assistance. That's where you enter $5250 (not $8000). Review the 1098-T, sometimes the school (erroneously) puts employer assistance in box 5. The short cut is to enter the 1098-T with $2750 in box 1 and box 5 blank.
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