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Something I struggle with every day. My guild has been around since day 1 of WoW and has grown/shrunk/transformed/evolved many times. We've touted being "casual" yet struggle to produce efficient raids, though we are currently on the upswing. We combat each other internally over this struggle as well; drop old content off the schedule and leave our newest players with no experience or gear from those instances, so that we may focus our efforts on progression? Or continue to run old dungeons, and cause resentment and burnout among our vets?
One thing we have done is open up more raiding nights, and we do our best to bring people in to replace those people who cannot raid hardcore 24/7. We have exactly the same types of people you refer to: People that can raid all the time, or some of the time; people who are the best on the server, and people who are sub-par and will always be sub-par. By opening more nights up, we continue to progress, and hopefully maintain a larger pool to keep those nights moving progress forward.
Pre-TBC, we opted to keep running old content. The result was this: We ran 2 or 3 generations of raiders through MC; 2 at least through BWL. But we never moved past Huhuran in AQ40, and we only succeeded in clearly the spider wing + Razuvious in Naxx.
This time, we are opting to drop old content off to focus on new content, with the hopes we will make it all the way through Illidan. I'm confident we will. And if there's time to spare, I hope to take people back to AQ40 and Naxx for fun. This is also something you can do for your guild to help keep them interested and keep things fresh.
Another thing I would suggest is using WWS to help get your guild conversing about their performance and what they can do to improve. When it becomes interesting to tweak, and outperform each other, you'd be surprised how much easier content becomes. That, in my opinion, is a far more rewarding way to encourage your guild instead of forcing them to farm for mats in their off-hours and demanding they show up flasked or they are removed from the guild. We have open discussions in vent and chat about what we observed...while other guilds on our server kill Hyross...and all 25 of them immediately log off...which is bizarre to me.
Keep in mind that if you continue to recruit (as we did, pre-tbc) to fill holes, make it perfectly clear that new recruits won't have the opportunity to run old content; you are moving forward and focussing on progress...and they should be geared appropriately to compensate (hopefully, crafteds make up the losses you incur by going this route). Otherwise, you'll simply run out of time and (as we did) only make it 1/3 of the way through the content you want to.
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