Rather then overfill a comment, I'll just take my responses to yesterday's and go in depth here. Thank you Logtar, Kadomi, Mookey, and Bent, for your long/insightful comments!
Kadomi's guild has cleared Naxx 4 or 5 times, and is raiding every weekend. She's thinking about how her guild should deal with farm raids, Malygos, OS, and Ulduar.
Kadomi - I would definatly clear Malygos first. Have your guild kill every T7 boss, collect your titles, then dive into Ulduar. OS+Drakes may just be something you need to cut out at this time. You can gain many of the skills it teaches in Ulduar - it'll just put you behind in some areas compared to guilds that could do that learning pre-3.1.
Don't take a wipefest in Ulduar on your first night/week as a bad sign. Luckily, you'll 99.9% (repeating, of course) be able to do Flame Leviathan+0 your first night in, which should start to get people pumped. After that, hit up Razorscale / XT, Iron Council, Kologarn.
I would say drop Naxx completely. If you really feel like you need a farm night every now and then, take every second/third week, clear Naxx & farmed Ulduar bosses. But as soon as you feel people are feeling done with Naxx, dump it like a green.
Mookey is the leader of a 25-man, 3/day a week guild, who looks at epics per hour, and different progression paths...
First off - thanks for posting! I love seeing new names in my comment section.
I wouldn't give your guild the title of "casual" - its allready a widely (mis)used word, and I don't think its fitting for how your guild sounds. LOKI is a 3 night a week guild as well (3 hours a night), and we too are simply serious about how we use our time.
If you look at Ulduar gear - many classes don't have upgrades (rather having minor upgrades or sidegrades) for many slots. I don't think that nearly as much gear is needed to get raiders geared (or overgeared) for T8, as it was for Naxx. By the end of Ulduar, if your raiders are mostly in 226's, you'll be awesome for T9. Just think of how many enduring pieces of gear there were from T4 (Dragonspine Trophy, Pocketwatch & Aldori Legacy Defender to name a few) that didn't get replaced in T5.
You also mention "inevitable need that you kill all bosses at least around 10 times in order to make everyone happy". Don't necessarily associate getting loot with making people happy. There are lots of people that would kill a boss only once ever, and move on, if it was possible. Ten kills certaly borders on the point where even people that are missing gear will be getting tired of doing a boss, and want fresh content.
They layout of Ulduar, and skippability of bosses, certainly is a boon. I definatly use Razor/Ignis/Council as rewards for progression, but am carefeul to not do them as the result of frustration on progression. Last week, we didn't kill Mimiron until a half hour from the end of our last raid day. Razorscale, Ignis, Council, Hodir, Freya, and Thorim - all bosses we've killed/farmed, went unkilled that week. If I had said, at any point on our 5-6 hours on Mimiron, "hey lets go do something else for a break" - I dont' think we'd of gotten the kill. When raiders know that they can get loot without doing the hard progression, they slack. Its just human nature to go for the low hanging fruit, the easy epics, the best loot per hour. But when you have to decide where to alot limited time resources, and your truely progression focused, you have to make hard calls, and hope that your raiding force believes/trusts you enough to follow you.
As for your Naxx run - an offnight alt/trial-including night in Naxx is a fine idea. "Best possible time investment" may be a strech, if your feeding the majority of the drops to said alts/trials/disenchanters - but if its all done in time outside your normal raid schedule, then by all means.
Walls of text, by the way, are encouraged and appreciated. Inspiring / making people think (readers and myself, alike) is why I write, and the things people say make me more thoroughly reevaluate my own thoughts.
Bent - The difficulty jump is certainly pronounced. T4 -> T4.5 was rough since it was a transition from 10 to 25 man raiding, which changed the dynamics of raid composition, assignments. T7 -> T8 is hard, because T7 was arguablly one of the easiest tiers released (as may be witnessed by the amount of people doing the content), and T8... isn't.
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