Ultimately, we don't know if she's improving, but she's been around since before she was hired as Pippa. From all the info her life was real shit before, and now it's basically just alright if you're being optimistic. Though there's a lot that really makes it promising like her becoming a sort of face for some new technology a partner company previewed that introduced augmented reality at a convention:
Why would she retire? I don't think she's seeking some kind of fame, she just likes what she does and her best content is mostly interviews with random game devs (she had a couple former Blizzard people on) and the like where she presses them a bit with questions.
This is what I don't get about the people who think she's just in it for the clout or whatever, she went from being destitute to being able to make rent consistently, and now she gets to interview people who actually have a name in various industries, and she's participating in a tech start ups that are doing some cool stuff with augmented reality and while it's not that exceptionally impressive in their techo demo where she appeared, it's some rather interesting stuff. I just don't see what's so wrong about someone having a passion, following that passion from living in a slum to actually having a real chance of breaking out and being successful as a bad thing. For all we know at this rate she'll be running her own thing instead of just being a talent hire at a company which she is now, because she does have an aptitude for business and talks about how she wants to grow beyond where she is now.
That's the appeal really, because sure she talks about lolcows, but there's a real drive there to do something. When she had some American "idol" on as a guest, she basically told her either the scene gets some standards and works to improve their situation or they die off like any other clique. The interviewee cried a bit but agreed.