If I were to have to go back to high school, I'd OF COURSE have several demands. I'd go back for little to no money, but I want to keep all the knowledge ("knowledge") I've gained since I last roamed the sacred halls of Kettering Fairmont and actually? While we're at it, I don't want to go back to MY high school. I want to go to a better high school, a shinier high school, a more magical high school.
That's right, I want to go to Hogwarts. I mean, aside from the occasional Death Eater invasion, who WOULDN'T want to go to Hogwarts? Hello! Everything is MAGIC, from the food to the staircases to the FLYING EFFING BROOMSTICKS.
I would even go back for free, if it meant I could make out with Oliver Wood (heh, WOOD, also sorry, Joe) and learn how to FLY AN EFFING BROOMSTICK. Hell, I would PAY to go there. Only, you know, I wouldn't pay a lot but only because I don't have any money. HOWEVER, if I could convince Abigail to give me some of the 20 mil she got for going back to high school, I'd totally pay a lot. What can I say? I'm a giver.
Honestly, I would only go back to high school if it was fictional. My high school experience wasn't a bad one, but I had so much more fun once I left high school that I can't imagine going back. So fictional is the way to go. This seems to be a running theme.
Other fictional high schools I would go to:
The high school in the tiny town from Footloose, so I could learn to dance.
The high school from Heathers, provided I wasn't one of the victims, so I could give Martha Dumptruck a hug.
Sky High (shut UP, it's a cute movie and OMG IT'S A SUPERHERO HIGH SCHOOL), UM so I could be a superhero.
Whatever high school Ferris Bueller went to because DUH I want to hang out with that guy.
Bayside High School, so I could kick Screech in the nards and give AC Slater a haircut (and convince Kelly not to break up with Zach for Jeff the Flaming Turd).
Sunnydale High, as long as I didn't get eaten by a vampire or sucked into the Hellmouth.
Back to the Future High School (whatever), but the future version, so I can steal a hoverboard for Heather! Anne!
Wayside School because, while not a high school, I've decided it counts. Mostly I decided that because I love those books and if that's not a good enough reason, I don't know what is.