Snake has been interpreted by a lot of fans as having an inferiority complex and deeply seated self-esteem issues due to his blow up towards Wolf during the third act, which often is used as a conflict in Wolf/Snake fanfics.
After the Plot-Mandated Friendship Failure with the Bad Guys, does Diane understand that Wolf didn't open up to his friends about being good and thus feels bad that he seemingly betrayed them, or does she think that it is good for him to 'cut ties' with his friends to join the good life, like what Marmalade told Wolf before? While Diane does assure Wolf that if his friends are real friends, they'll support his decision, it is ambiguous whether she personally believes the Bad Guys are True Companions, or that they hold Wolf down, like what Snake fears.
Did Marmalade always intend to betray Snake at some point to get all of the bounty from his heist for himself, or did he genuinely want to strike a partnership with him until he changed his mind at some point?
What is Tiffany Fluffit's personal opinion of the Bad Guys? Is her negative coverage of them motivated by prejudice against scary animals, or is she just echoing widespread sentiment about them to tell people what they want to hear and get herself more ratings? If the former, is her praise of them during the gala a genuine change of opinion, or does she still secretly fear them and only change her tune to keep up with public opinion?
Is Mr. Snake's strongly adverse reaction to finding out about Wolf's planned Heel–Face Turn really because he feels that Wolf is selling out the gang? Or is it because Snake himself had been planning to do the same thing with Marmalade and was envious that Wolf beat him to it, meaning he'd get the credit for being the first of the gang to reform before Snake did? An earlier conversation can even contextualise it as being more upset that Wolf didn't just tell him his intentions when he asked him about it, feeling hurt that his closest friend didn't open up to him.
A lot of Diane's development in behaviour throughout the film following The Reveal she is the actually the Crimson Paw can be recontextualised as her either slowly coming to trust the Bad Guys' change as genuine (and maybe even trying to instigate it in the first place), or her learning to curb her own ego from being a master criminal herself, and not call the kettle black, or possibly a bit of both. In particular:
She trash talks the Bad Guys in her live statement and is hesitant to approve the redemption scheme over throwing them in jail after they almost get away with the Golden Dolphin. She can be interpreted as either wanting to double down on undermining and preventing dangerous threats to the city to make a good first impression as Governor (thus her annoyance when the Bad Guys make a fool of her in public), or tacitly bragging about her own success rate, and then acting like a Sore Loser when a supposed pretender outsmarted her, deciding not to underestimate them again. A third road is that she provoked them on purpose, fully expecting them to go after the Golden Dolphin as revenge, and inevitably get caught.
After the disastrous guinea pig heist, she threatens to abort the rehabilitation and yells at Wolf, until he snaps back over all his demons from being a villain and no one giving him a real chance, causing her attitude to soften. Given her triumphant look during Wolf's tirade however, it's easy to interpret that Diane was calling his bluff and intentionally goading some sign of growth out of Wolf so she could trust him at last.
Her handing her ring to Wolf as a test of character following The Reveal it was the Zumpango Diamond she previously stole. Was she shrewdly demonstrating a deep gesture of trust to Wolf, or was she pawning off a stolen item to him, with the potential of framing him as the Crimson Paw if he tried to betray her? After Wolf finds out, is he amused she was that cocky with incriminating evidence (thus not so above his league as she boasted), or more impressed she played such a dupe on him?
Was Chief Luggins at least a little sincere about the possibility of her not having an identity outside of catching the Bad Guys, even if she didn't realize it? In the Maraschino Ruby short, she actively attempts to bait the gang into stealing again, but this could also be paranoia and her wanting to catch them before they actively do anything bad again.
