While I'd love to try this again now that ORAS are around the corner, I still fear the biggest roadblock is the fact that we have kind of serious, high-powered teams that scare off most people who aren't willing to breed and train their own competitive-caliber pokemon. I frankly think there's just no way for people playing through the main game to stand a chance against the gyms unless they went for the cheapest strategies they can find to counter their type specialisations, which wouldn't be fun for either party.
If we intend to make the league a healthy environment, we'd need a constant influx challengers. Since those who get the badges don't need to get them again, someone who has beaten all the gyms would basically have nothing else left to do, which is something we've got to fix unless we want to end up with no players once they've all earned their badges or given up after losing repeatedly. After seeing what happened with the league last time, I'd say the whole gym concept is broken, simply because it doesn't take into account that a healthy environment needs to keep the players playing, rather than have them beat a gym, get the badge and be done with it for all eternity.
I think the best way to make a better environment would have to do with weekly tournaments imposing some type restrictions (i.e.: you represent a type of your choice and need at least four mons of that type in your team) or some other things of the sort, since the whole gym idea left us with eighteen players who could only take challenges and just a handful of people who actually decided to take us on.