It took Vaggie a few years to regenerate her wings, and even then, it was only when she did her dance-fight with Carmilla, so it seems like angels can only regenerate when they aren't dealing with psychological trauma. Of course, I'm probably just making up excuses that the writers never thought of.
That's something that's done in Steven Universe with Volleyball.
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Steven couldn't figure out how to heal her cracked eye because it was a psychological issue and not a external issue. Meaning the only way to heal the cracked eye was to confront the fact that Pink was an abuser.
I think a lot of these worldbuilding problems come from the show itself asking questions it's not equipped to answer. It's extremely hard to talk about redemption when you treat harm and care inconsistently. For contrast, instead of bringing Sir Pentious with them (or at least proof he's up there if even angels can't get him down), Heaven's ambassadors brought gift baskets. An easily exploitable move given the context, and one that Vox took advantage of. Yet in the pilot we see Hell cleaning up its dead immediately, eating parts, picking them up to sell, Rosie crossing off her business partner's name. I haven't forgotten that disabled kid in Helluva Boss, or Vox using a kid as a prop. It all makes you wonder what Hell actually values.*
If Hell is some open air prison where people still love children (not like that) in the cold depths of their hearts, it'd be believable and looks like the direction it's going for. Yet the sinners that do get focus... don't have reasons to leave except Angel Dust (and Cherri maybe). Even Husk still owns a casino. A lot of Hell's corrosive aspects are either punchlines or background noise. The plot circles around this with the whole war with Heaven, because the only reason they'd want to leave is to not die, which can easily be stymied by closing the loop with Heaven and ending the seven-year-old extermination tradition. I think Vivzie knows this deep down on top of not wanting to kill her darlings by changing them.
To bring this back to Vox and how power works, *a lot of evil comes from belief. It can convince itself it's doing good. It's possible that Hell's power doesn't rely on true power as much as the belief or appearance of it. While this could explain why ratings and the like affect Vox so much, it also aligns with the likes of Rosie (leader of cannibals) and Alastor (repeatedly earned street cred) having so much power in the first place. But it also raises the questions of: what about the sins and Ars Goetia? Are they fueled by both sinners and earthly wrongdoing? Or are they just naturally strong due to their divine/demonic natures? Bee mentioned about sin in her circle fueling her so I guess it’s the first to some extent?
Steven Universe solved a lot of its power issues by having both body and ability reflect the mind in the gem along with its "model." That does apply to this Hell, with sinners' bodies reflecting their lives, deaths, and personalities, yet making power innate instead of built undercuts relying so much on networking, perception, and social standing. However, it'd cut the Gordian knot while emphasizing agency.
