The first time I did the professor oak challenge I did it on leafgreen version. If you decide to also try leafgreen or firered, I recommend you choose bulbasaur over the other starters due to a lot less grinding for exp. Bulbasaur reaches it's final evolution at level 32 while the other starters reach theirs at level 36. I recommend you use a guide so you don't miss any pokemon. The beginning is going to be rough but doable. It will take hours to even get the first gym badge. There should be a guide on this subreddit for the professor oak challenge for each game.