Flogging a dead horse

Last night, my guild did Kara. In itself not an unusual occurrence for a Friday night.
I was mucking around in SMV on my druid, and the got into a group for Magister's Terrace (which broke up as 2 people went to do kara, go figure) and then did Isle of Quel'Danas dailies. During this period of about 1-1.5 hours my guild had been doing Shade.
That's quite a few wipes and obviously stuff was going wrong. Eventually someone left to go to sleep and I got called in. Now I had been looking forward to doing a bit of kara on the druid, but if they'd been wiping that often I wasn't sure how much difference I could make. My druid had only been 70 for 3 days or so, and my gear was pretty bad. I could have brought in a comparatively well-geared hunter who has downed Shade and knows the fight, but apparently the guild wanted "more heals", for a total of 3 resto druids and a holy paladin. How much +heals did I have anyway? About 1250 or so in my mostly greens-and-blues, but that left me with about 6.8k health, not quite what you want on Shade when you can't get PW:Fort. So time to swap in the triple-Solid Star of Elune Heavy Clefthoof Vest. A bit better, although the heals did dip.
And then it was off to Moonglade to find out what this "Tree of Life" thing was all about. I had never been resto before. Moonkin from 40-48, and again from 62-64, but otherwise levelling had been solidly Feral. Which is not to say I hadn't healed before: I'd tanked or healed every Outlands instance up to Old Hillsbrad (after which I focussed on levelling) and had done a reasonable job of healing (although my tanking skills leave something to be desired). But I'd never healed as resto, and never healed a raid. Is this undergeared, inexperienced Druid what you want in a fight that you've been wiping in all night (or rather a hunter that brings another 800-1000 dps, plus Snake Traps)?
So all of a sudden I had leaves. And Swiftmend. And no addon for raid healing, so had to just drag health bars all over the UI and hope I knew what I was doing (I didn't).
At least I knew the fight: don't move during Flame Wreath, and shift out of tree during Arcane Explosion, etc... on the other hand I didn't do much. With my crappy gear my Lifeblooms couldn't do much and my Regrowth would always land 0.5 seconds after the Paladin's Flash of Light. It went ok until someone (not me) moved during the second Flame Wreath, after which we called it quits, to general calls of "fuck Shade".
Now I didn't want to go back to questing as Resto (who would?) so I was looking at 60 gold of respecs in less than an hour, just for the sake of a wipe (at least it's not 100g, but I see that coming up soon). So I did a single AV (for once we completely and utterly dominated, to the sum of 630 bonus honor) and then Teleported back to Moonglade to get back in touch with my inner Kitty self.

So basically what I was building up to: if you're going to be wiping on a boss that you know for several hours in a row, why not just skip him? Sure Shade controls the respawns in the Library zone, but if you're not going to down him, wouldn't it be better to move on up and just clear the spawns again on the Sunday run?
I'd say if you wipe three times on a boss, and don't come close to winning at any point, then you should seriously rethink the strategy, the group, and consider calling it quits for a while. Especially when the boss is optional.
And obviously you're doing it wrong. I mean nowadays Kara can be cleared by people in quest blues and greens. Our final Shade attempt had 2 people in full epics (combination of T4 and T5 equivalent), and on average more epics than blues.

Anyway, I have a house that needs to be cleaned on this fine Sunday morning.