Not sure if other guilds have to deal with this sort of thing, but Ulduar, strangely, has been a chore in keeping folks happy.
Naxx was a little bit easier in this regard. The only way to get to KT was to clear the whole damned place. Sure, we could mix it up by starting in different wings but eventually the place had to be cleared. Further mixing up could be done by chosing to start the night with OS or Malygos instead of Naxx or any combination of the three. Despite how tedious that got, I look back on this and realize it had some merit.
Ulduar has optional bosses. This is not unlike some other instances seen before (Kara was a good example of this) but it seems a little harder to deal with in Ulduar. This is because some BiS items are off those optional bosses in either hard mode or regular mode. Throw in different raid compositions from week to week ( or even day to day) and things get a little muddled.
For a while there, every week I had some folks ask me why we were spending time on optional things when we could spend our time on bosses we haven't cleared yet. Other people asked me why we were skipping these easier optional bosses when their upgrades were on them. Sometimes I had the people ask me the same questions within the same raiding week which made my head spin. Seriously? You ask me why we aren't doing the "gear up" bosses then ask me why we aren't working on harder stuff? Shoot me now, please.
Then factor in the definition of "progression". Is progression downing the hard modes or clearing the whole zone? Is progression gearing up every member of the raid with BiS or making sure they all have t8? Ask 5 raiders and I think you might get 5 different answers or all of the above at the same time.
This makes it very challenging when deciding how to plan our raid nights. We go in with a general idea of what we would like to see accomplished but we also have to be flexible. Last minute back outs or sign ups throws things off a little. Some nights we have too many healers sign up and some nights we lose our MT. Other nights has our core dps lacking so we give our new recruits a shot.
We got really lucky and had some new raiders join our guild. I always cringe on those nights they join us not becuase of their performance but ours. I am always concerned about making a good impression and showing how we really roll. Catch us on a night where things just don't click and I start to sweat a little. I am learning to get over that but it's still a concern for me.
What has been slowing us down a tad lately is having to explain the fights to these new guys. Yes, it's needed, but tends to make people fall asleep. During these explanations folks seem to want to take this time to ask random crap over vent that could be said in tells (and by folks I mean officers who should know better). Just because you understand what's going on, doesn't mean that random interjections aren't screwing up the new folks from absorbing the information they are trying to get.
But I have to admit, our new guys are awesome. The strats are watered down or filled with holes (Oh yea, did we forget to mention how Phase 3 of Thorim worked? Sorry you died to lightning), but they plug along and do their best. Low maintenance recruits ftw.
Again, everyone has their own definition of fun. Most folks agree that banging our heads against the wall on bosses tends to suck the fun out of a raid night. I personally like wiping in catastrophic ways. I don't know how many times I have laughed my ass off after dying to random ability no. 104 because either it was unexpected or just play from my own stupidity. Granted, I am not so fond this when it happens more than once or other die to it after I just said "Don't be dumb like me."
But Fun and Progression tends to cross into the same territory which brings me back to the same evil cycle. Keeping raiders happy is always a careful thing to handle and sadly it doesn't always work or happen the way it was intended to go.
Next week we plan to cull some of the crap and go for serious work on the General. We have a large chunk of our raiders going on an annual trip which puts a little pressure on us to get some work done. Maybe folks will have fun. Who knows?