I generally do not play canon characters well, but given my significant familiarity with Winnie Foster’s character and the fact that she is basically a mash of all versions aged over a century, I think it’s pretty flexible with characterisation.
Funny thing is, I think she might become more like Miles, because she lost her family. She was married to Hugo Jackson and had a child. She met Hugo when he returned her home after her adventure with the Tucks. She was the only person she shared the information about the spring to, all except location. So when she fell fatally ill, Hugo couldn’t bare to lose her. He searched for the spring, found it, and tricked Winnie into drinking from it. He was aware that she had decided not to, but her survival was more important at that time.
Hugo had planned to return to the spring later with their child so they could become an immortal family as the Tucks had been, but Winnie prevented that. Once she had discovered what had happened and had figured her plan, she filled in the spring to prevent anyone else from drinking and being cursed with immortality.
Hugo and Winnie never saw eye-to-eye on this. Winnie didn’t wish for her family to be cursed as she was Hugo believed Winnie did not want to be with them forever, wanted to run off and find the Tucks again. So Winnie left, as she would have had to, to prevent suspicion. The official story was that she had travelled to a more tropical climate to relieve her illness and never returned, though her grave is found at the Foster home. Only Hugo knew what had actually occurred, even the child was unaware.
So Winnie is now in a similar but opposite situation as Miles. Common ground could be found. I imagine she would despise Jesse somewhat, for making her think that immortality was a wonderful thing and trying to get her to drink for his personal gain of her company.