Okay, let's answer this now that the season's over.
Cinderella (S1 - S6) vs. Cinderella (S7) - This truly saddens me because I wanted so much to love Dania Ramirez's Cinderella, but the writing was just so bad and her storyline was left feeling underdeveloped and incomplete. At least with Jessy Schram's Cinderella I loved both centric episodes and felt like we were told a complete story with the character.
Lady Tremaine (6x03) vs. Lady Tremaine (S7) - Lisa Banes was the perfect Lady Tremaine and made for a very memorable episodic villain. Though I came to like Season 7's Tremaine, Gabrielle Anwar never fully grew on me, and I liked her more for the Rapunzel aspect of her story.
Clorinda or Tisbe (6x03) vs. Drizella (S7) - Drizella was one of the best additions to Season 7, and Adelaide Kane put on a hell of a performance. I fell for the character instantly and fully enjoyed her until she departed.
Clorinda or Tisbe (6x03) vs. Red Queen (OUaTiW) vs. Anastasia (S7) - There's really no debate here, the Red Queen outsold in every way. Do I even need to explain myself?
Alice (OUaTiW) vs. Alice (S7) - This is a hard one because I love both of them, but I wound up loving Rose Reynolds a bit more. Easily the best part of Season 7 for me turned out to be the new iteration of Alice, from her dynamic with Rumplestiltskin to her love story with Robin, the character always had something interesting going on, and Rose Reynolds brought some much-needed energy into the show. That said, while Reynolds' took a more unhinged, batshit-crazy approach with her Alice, Sophie Lowe managed to successfully carry the short-lived spinoff with her own take on Alice: a badass, but still elegant, warrior who does not always get the credit she deserves from the rest of the fanbase.
Fairy Godmother (1x04) vs. Fairy Godmother (7x01) - Neither is particularly good, but I find 1x04's more memorable with it being such a shock that Rumplestiltskin murdered the iconic Fairy Godmother. When Lady Tremaine did it in 7x01, it just felt overdone and like a missed opportunity to finally make her into a real character.
Prince Thomas (S1 - S6) vs. Prince (7x01) and Henry Mills (S7) - Henry getting to be Cinderella's prince was a cool take, even if the storyline itself turned out to be a dud.
Rapunzel (3x14) vs. Rapunzel Tremaine (S7) - I love the twist with Rapunzel growing up to be Lady Tremaine. It was clever and felt very much like the old Once Upon a Time, which I really appreciated. I loved Meegan Warner, and it's because of the 7x09 backstory that I was finally able to appreciate Anwar's portrayal of the character in the present day.
Charming as Rapunzel's Prince (3x14) vs. Wish Hook as "Rapunzel's" Prince (7x07) - They really learned nothing from all of the backlash over the Zelena/Marian/Robin fiasco of Season 4.
Manifestation of Rapunzel's fear (3x14) vs. Witch/Mother Gothel (S7) - This is just me being petty because I absolutely despised Gothel. She falls among my least favorite characters of the entire series, and I spent all season just waiting for her storyline to finally be over.
Jack (2x13) vs. Jack (S7) - I like the twist with Jack being a woman, whereas Henry's underdeveloped bromance in the NEF did nothing for me.
Blind Witch (S1 & S5) vs. Hilda (S7) - Nothing but love for Emma Caulfield, both in 1x09, her stint in the Underworld in 5B, and of course her years as Anya Jenkins in Buffy the Vampire Slayer. Meanwhile, I have zero memory of Season 7's iteration of the character.
Robin Hood (S2 - S6) vs. Robin (S7) - I hated the original Robin Hood and Outlaw Queen and was relieved when that storyline was finally put to rest. Meanwhile, despite not being sold on Tiera Skovbye's acting, I liked seeing the character's dynamic with Zelena and love story with Alice (and it helped that Rebecca Mader and Rose Reynolds were talented enough to carry the scenes on their own). Mad Archer was one of the best things to come from Season 7.
Gretel (1x09) vs. Gretel (S7) - I actually really liked 1x09 as an episode, and I remember wishing 7x15's flashbacks were focused on something else.
Hansel (1x09) vs. Hansel/Jack (S7) - My jaw literally dropped when Zelena burned his arms, so I'll give him points for that.
Woodcutter (1x09) VS Ivo (7x17) - His relationship (if you wanna call it that?) with Zelena felt random, but I was actually into it.