Assuming the student is your dependent and you are the recipient of the 1099-Q:
Enter the 1099-Q before you enter the 1098-T. TurboTax will only give your the R&B screen if it knows you have a 529 plan distribution. Later, in the 1098-T (educational expenses and scholarships) interview, answer yes when asked if you have book expenses. That screen includes the box to enter Room & Board.
