Not on here often at the moment, but I like to check in on this and a few other threads when I can. Apologies if I am resurrecting a dead conversation but, well...
My thoughts on past/present Tiffany:
Young Tiffany already has reason to care for the MC. He saved her from being assaulted, probably saved the life of her future child, and has treated her sister with nothing but kindness and affection (and some requested and fully consensual depravity, which she may or may not know about). This is a solid basis for more intimate relations.
Tiffany does not have a boyfriend. She has an ex. There is no moral obstacle here.
I don't know if we will see something between past Tiffany and the MC in the next update, but if we did, I feel it will fit very well with her character and their relationship progression.
I understand that some people have a view of Tiffany that is based on her present relationship with the MC, where to them any difference in pace for past Tiffany would feel wrong. But this should not affect the way the story is written. It is the author's conception of the character, and whether the character's actions make sense in context of the story.
It's important to separate past Tiffany and present Tiffany, because in the context of their relationship with the MC they are different people. Young Tiffany does not have the same relationship with him as current Tiffany, so holding that relationship to the same standards is invalid. And young Tiffany getting with the MC does not change the slow build with present Tiffany in any significant way. I don't think it would affect the present other than facilitating present Tiffany's acceptance of what she wants. It's one more small nudge, not a sudden 0–100. She's still the same woman. He's still the boy she's been raising like a son. Realising that she did something with him in the past (which is almost inevitable, no matter the time it takes to get there, and from a present perspective has already happened) isn't going to change the rest of their history together.
I trust that Jestur has thought about this. He went to the trouble of rewriting part of Skylar's story to slow it down because he thought it had gone too fast. I was okay with the original speed - it seemed in character for her - but the rewrite worked as well and I have no complaints.