I do understand the hype around Winter Verdandi, but he is ultimately just straight up a bad match for Penelope. The appeal of Winter is that he is a good person. Of everyone, he is the only one defined by his kindness and desire to protect others.
Re: Winter testing Penelope. It is entirely justifiable for him to do so, and he ultimately does it without ever purposefully putting her in danger. Winter is a good person with something to protect, and that's why it's difficult for me to feel any real anger towards him for what he did. The problem with their pairing is that Penelope is a desperate, self-interested person.
Maybe in a different story, this would be the foundation for a strong push and pull between Winter's selflessness and Penelope's selfishness, but in VADD, Penelope's laser focus on her own survival does not leave room for that tension. She never ever falters. Her priorities never waver. Romance with Winter is never on the table and, unlike other FLs, as soon as she realizes he isn't of use to her, Penelope pretty much completely ignores him in favor of pursuing her safety. She doesn't trick herself into thinking it'd be beneficial to lead him on or maintain a relationship. She doesn't invent excuses to see him.
There isn't time for romance or chemistry to build between Penelope and Winter because she straight up doesn't care about anything that doesn't threaten her safety or secure it, and Winter happens to perfectly land in that spot. As a good person, he will never purposefully hurt Penelope. As a good person, he will never save her either. So why pay any mind to him?