For 1098-T Do I enter 1/2 amount of box 1 since received & paid for 1 semester in 2018? Or entire grant & payments for academic year 2018-19 as listed on 1098-T?

Box 1 is supposed to report what was paid in 2018. 

If box 5 has an amount of aid that will apply in 2019, select that answer (scholarship allocated to a different year) in the Scholarship Interview. 

What do you mean select that answer for box 5? Box 5 has the same amount entered as box 1. I guess the college considers that they gave all the aid in 2018 even though 1/2 of it was deducted from the spring (2019) tuition which was paid in 2019?