As a rookie SNES player, now awaiting my sophmore season, I have limited experience with these leagues, but I'll share my opinion.
I really enjoyed the structure of a real season that the Classic league gives. I agree with chaos's analysis. IT would be fantastic to have a matchup based deadline system. Say, every week you have to play a pair of games against three particular opponents. This will force the players to keep in touch more regularly and plan their schedules ahead of time, instead of playing whoever whenever, all the time.
It will also keep the regular season schedule in check. So that the situation is avoided when a few teams have finshed their season while the rest struggle to catch up because of a few "poor connectors" (ie people who don't meet deadlines and don't reply to IMs, etc.)
The season will be slower paced for some, but would run its course over the same period of time or possible in less time, as it would be more efficient.
I think what the league needs for newcomers, both during a season and all year round, is a competitive ladder system. This is most often used in Tennis clubs. You could Goolge "Tennis Ladder" for more information if you are unfamiliar. We could have two ladders, one for for each general skill level, or even just one ladder reserved for players who want to improve their skills.
Another tactic would be to set up some kind of AIM group, so that newcomers can easily join into a big pool of players. This giving them more opportunities for exhibition games. I'm not sure if this is readily possible, or if it means that the whole league has to be more aware of new players so that we can all add them quickly. Maybe Halifax can send a mass IM reading something like this: "New SNES (or GENS) player, AIMNAME. Add him (or her (LOL!))"
All in all, having gone through one season, I think the total experience is great. Although there is room for improvement, for the most part, the league runs really well. So keep up the great work.
Thanks and peace.