This contest was a test to see how well the idea went. As we know, Heretic and DD are both amazing writers and RPers.
That said, The reason I voted for DD are below.
While Ask the Heretic had a better grasp of the background lore via her judgment, I felt she did not really convey her relatioship with Leona very well.
The ending of her judgment made no sense to me. If Leona and Diana met right after in the ruins, it would have been their final battle then and there. In Diana's lore, Diana walked away from the temple as it fell into ruin. Leona was not there.
Heretic also had a better grasp of the dark stotic nature of Diana, but we didn't feel the raging emotion underneath very well. On the other hand, DD was a little 'too' emotional.
Dear Dìana (the one with the weird i) was able to interact wit the other champions better, and tuthfully, it was nearly at a stage of heretic and DD being a tie that a coin toss was being considered.
Both are amazing, and both deserve to be Diana. The last series of question by Grand Viper was what drew the line. We felt that Dear Diana anwsered the question just a little better, which gave her the advantage.
I think that toneing down the emotion of DD would make her the prime candidate.
But with all Asks, remember, if Dear Diana neglects her duties, she will open up in the future. And at that point, I do hope Heretic would be able to jump in and fill the role.