About OgPenelope and Vinter meeting, I have some thoughts.
Imagine it would be a very slow burn thing with them. With OG Penelope being wary and distrustfull of him at first due to Eckhart's treatment of her.
Meanwhile, depending on what kind of meeting they have, Vinter would have different reactions. I could easily see Vinter noticing her sadness, and having a scene similar to the story where he tries to comfort her, although she would likely refuse him.
I keep imagining he still trying in gentle ways to look after her, and OG Penelope having a sweet scene where she gets to be happy watching the magic bunnies. Consider a sweet scene where Penelope looks in wonder over magic, one that resembles fireworks, one that doesnt hurt her, and Vinter feels touched over her love for magic and happiness around it.
Another idea, would be they both looking or trying to aid orphans, as Penelope, who had been in their place before, would likely advocate for them as well.
Some ideas, feel free to disagree with them though.
I apologize for the late response
I see them having a slow burn due to many reasons, one of which is lack of trust as you mentioned. Penelope will find it difficult to open up to Winter because of her unpleasant experience in the duchy, Winter who notice this will patiently wait for her to open up because he's afraid that he will scare her away.
It is also possible that Winter has a bad impression of Penelope because of her bad reputation and her attitude but as they get to know each other better, Winter will see her in a different light and maybe he'll show the other side of himself that no one knows and will feel comfortable sharing the deep secrets he had been keeping.
Seeing Og Penelope helping Winter to help the orphans was so cute and heartwarming Because like you said Penelope was an orphan before so she can easily relate to the orphans in the slum (I can imagine her feeling a little bitter because she'll remember her awful past but I think this will also show her soft side) plus it will be a big help to boost her reputation among the people.
Speaking of magic we all know that Og Penelope is a descendant of ancient magicians(spoilers for those who don't know). I'm imagining what if Winter taught her how to use her powers properly it would be cool.