>>116464109Olga is actually Oleg, a Trans-passing male to female. She is still hyper competent and super successful, still as a result of the soul crushing pressure to perform.
Helga resents Olga not just for being successful but for stealing her attention as being the family daughter.
Bob unintentionally deadnames Oleg all the time because he doesn't get it but supports it because it's "on brand" for successful business leaders to have Trans kids, and Helga's mom who's name escapes me is still a soulless woman trapped in a life she never intended on falling in to, and just sort of is excited that Olga will probably not be a burden on them.
Olga reveals to Helga in a moment of emotional weakness that she isn't really sure who she wants to be, and is actually jealous of Helga's lifetime of mediocre happiness. This comforts Helga who finally recognizes that, like Bob she doesn't understand Olga either, but unlike Bob she wants her sibling to be truly happy and knows she can't dictate what that means for Olga. They bond over an old picture of Oleg and Helga hugging as children.
In several subsequent episodes a point is made to show Olga crushing other women at local sports competitions, much to Bob's loud and obvious pride and the mother's stupified acceptance in short non-plot related vignettes. Phoebe is visibly annoyed by this.
This assumes a Hey Arnold! With the same mix if snarky evenly divided praise and criticism and not an ultra-woke parodyscape.