I've organized a new playthrough of the Pokémon games with my friends to try to get the most fun out of going through Gen 1, 2, 3, and onward. Currently, here are the (very simple) rules. Otherwise, it's anything goes.

1 - Every time a badge is earned, you stop all progress and wait for everyone else.
2 - A tournament is held once everyone earns the latest badge.
3 - Pokémon are are level synced to the latest "cap", then battles are held in Pokémon Stadium. No clauses.
4 - Prizes are awarded based on placement, including a special Pokemon lottery that includes Stadium rewards and other oddities, as well as ingame money and 10 Poké Balls.
5 - Repeat this process until we beat the Elite 4, have one final battle, then move on to the next game, retaining all Pokemon we've caught so far.

The results of the first tournament are in, and it was a resounding success. There was an upset early on with parafusion, and then a mirror match between Uni and Ocho's Bulbasaurs that went down to the wire in the loser's final. Do tell me what you think of these prizes for the first tournament. I tried to make sure they weren't balance breaking, but also make it worth it to participate.

1st - 10,000₽, 10 Poké Balls, 5 Great Balls, Pokemon Lottery (He won a Lv5 Gastly with Lick, Haze, and Confuse Ray)
2nd - 7500₽, 10 Poké Balls, 3 Great Balls
3rd - 5000₽, 10 Poké Balls, 1 Great Ball
4th - 3000₽, 10 Poké Balls

As far as the future, almost everyone has reported to obtained the Cascade badge, I'm just waiting on one more player before the next tournament is held. I'm thinking of making the next tournament a best 2 out of 3 kind of affair instead of 1 win = advance. I'll make sure to get a video of the next battles if anyone gives a shit.

I made a little graphic of everyone's progress so far circa when we defeated Brock. Hopefully you found this interesting, thank you for reading.