Firstly, extremely relatable post. Sometimes I wish I could go back to secondary school when all I could look forward to is going home, playing PS4 with my mates and watching my favourite YouTubers. Unfortunately, time does not go backwards and you have to embrace the future.
Figure out what you enjoy and what you're good at. If you're good at numbers, take up a numerical degree like Economics, CompSci, etc. If you're good at more verbally-written assignments, History or some sort of analytical field would be good. Then when it comes close to graduating, you should look at doing some internships, summers/weeks in a company to get experience so you can then apply it to the things you enjoy. And what you enjoy will always change so keep it close to you.
Being financially free is subjective to a certain extent, but if you have a good job (i.e.: you don't work retail or food services for the rest of your life), you will be mostly financially free. Though American educational debt is annoying, you will probably have enough income to enjoy things from time to time.
Now, Sliggy is indeed fortunate to be in the position he is in, but do not discount that he has worked hard to get where he is. He started off as a pro in CS:Source back in 2009 and was a coach in CSGO from 2015. Then he goes to Valorant and coaches pro teams until 2022. In basic terms, he has been working hard for a decade to maintain his presence in a volatile environment like the eSports market. He is now a streamer, but he didn't just sprout knowledge for the game. He has been consistently a thinker-type for years across games - and therefore, he has earned his comfort to stream Valorant pro games and get paid nicely for it. Bare in mind, he is also fairly new to streaming so he isn't raking in huge numbers, but he definitely gets a nice sum of money from his TL contract.
All-in-all, there is a lot of hard work you got to commit if you wanna be in Sliggy's position. And this goes for any high quality role, corporate or freelance. If you wanna be a streamer-analyst, start right now as a hobby to stream. Post your VODs or clips to all social medias. Build a brand and network with individuals.