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How about where you access an ultimate backup area with very powerful trainers witch you can have as many rematches with them as you want and a tournament.
I use kanto for place to get rare and beside that it was pretty boring and gyms were easy the only part i liked was mt. silver even though technicly its really is in the Johto.
Then explain Silver in GSC/HgSs. I think he could find a the back entrance in turnback cave and come out planning his revenge on Lucas/Dawn who he blamed for his banishment which he ultimately brung a pon himself and travels to the Isshu region where you and Lucas/Dawn team up against him.
1.get 1st and 3rd gen starters
2.collect Kyogre/Groudon and try to get Rayquaza
3.Get into the friendship room at pokeathlon
4.Collect all shiny leafs on one pokemon and get Lyra/Ethan to change them into a crown
5.Beat the battle frontier
6.Catch all the pokemon
After I beat Red I decided to defeat the Elite Four again go up to mt. Silver and defeat Red again over and over untill all of my pokemon are lv.100 so I can defeat the battle Frontier easy.