I think restorative nostalgia is the number one issue with comic book fans.
A fine distinction between two types of Nostalgia:
Reflective Nostalgia allows us to savor our memories but accepts that they are in the past
Restorative Nostalgia pushes back against the here and now, keeping us stuck trying to relive our glory days.
Honestly, I feel like the concept was extremely interesting and a perfect fit for Spider-Man. Since she effectively stood as being a physical representation of the whole "great power means great responsibility", dodging her hero responsibility, subletting her identity to her friend, who wasn't truly ready or prepared for what to expect, and in turn resulting in her death, so the guilt leads her to take up the mantle again. It's a shame they didn't do much with Sara after this beyond those couple Web of Spider-Man issues where she faced the consequences of re-emerging as Jackpot, since there was alot of places you could explore that character and that dynamic.
I only read a few stories at the dawn of BND with Jackpot. I thought it was fine as a character and plot to have a registered hero that wasn't as capable as the outlaw Spider-Man was back then. I never imagined she would end up being MJ, so I was fine with the Sara twist. I think it was a playful mystery with the audience. I'm indifferent towards her appearing again in a Spider-Man series. If a writer has an interesting story to tell with her, go ahead.
"The Batman is Gotham City. I will watch him. Study him. And when I know him and why he does not kill, I will know this city. And then Gotham will be MINE!"-BANE
"We're monsters, buddy. Plain and simple. I don't dress it up with fancy names like mutant or post-human; men were born crueler than Apes and we were born crueler than men. It's just the natural order of things"-ULTIMATE SABRETOOTH
Part of this too, I believe, is the inherent flaw of having a book with rotating writers as long as it did. Biggest flaw of the Brand New Day run for me personally was the lack of stability; each writer had a pretty clear preference on which supporting characters they favored. So any potential for the character got squandered due to the fact that Guggenheim was really the only one of the writers that had any plans for the character.
The artist formerly known as OrpheusTelos.
I'm not sure that Jackpot had much staying power, but I think more could have been done with both Alana & Sara. It would have been interesting if, for example, they hadn't stuffed Alana into the fridge and instead she'd gone back to her roots in social work (considering how big of a role FEAST was playing in that era), so she could become a friend to Peter and/or Spidey. An you would have a female character as a friend to Peter with none of the romantic baggage whatsoever, which would be a refreshing change.
Sara was kind of ruined by her own miniseries basically vindicating that she made the right call in hanging up the costume and ends with her going back to her home planet - I mean, going into witness protection.
But in both cases, if they found out Peter's secret id, you'd actually give him someone to commiserate with about the job that's not a preestablished hero that's tied up in other stuff, and that has a good reason to not just help Peter directly (Alana on account of her health, and Sara because she'd be unwilling).