Diane's update in .18 wasn't my favorite. I enjoyed Jenny's update, but she's not even close to my favorite character and that didn't change with her update.Yeah, Diane and Jenny really weren't the most popular updates and it was probably right to not continue reworking things for some time at that point. I'd personally hope the next poll will only include Judith, Debbie, Mia and Erik, so there's a good chance to either get an important rework or the last schoolgirl.
But yes, Debbie's update will indeed be painful. She's got a lot of content and basically all of her scenes (except for the threesome) are so old that they'll have to be replaced. So it'll be a huge update with, apart from her pregnancy, likely very little new content. Of course many thnigs will be changed, but just as in Jenny's and Diane's case, it won't feel new.
The last time I talked to DC before I stopped being a patron, he said that a Debbie re-work would only be a half update, but I agree with you. I think it will be a full update. It's just a lot of art work to conquer and pregnancy to boot. I think Roxy's and Debbie's are definitely the best stories IMO. I play Debbie's every time and I love it every time (although it was better with the incest dialogue, IMO). I know Eve's is super popular, but I wasn't a huge fan. Grace was my favorite in the story and there just wasn't enough of her.
For me Debbie's rework update won't be painful, it will be awesome. What's painful for me, is playing .20 and watching Debbie's new artwork and then it changing to the old artwork. It's very jarring for me.