In an earlier entry I complained about the sense of culture-shock for a casual player in World of Warcraft when you switch from the largely solo-friendly leveling grind to the explicitly group-focused endgame. Recently biting the bullet I decided it was time to suck it up and try and find a guild, else I really had no reason to continue paying any longer. I already talked about the endgame hierarchy; through level one to eighty a player comes across several "instances" which are more difficult environments that you run through in a group of five people. Monsters are harder to kill and they're more challenging, and as such they give you better rewards. When you get past 70, these instances start getting heroic versions, which are even more difficult to go through and require better gear and groups of characters at the max level. Heroics give you gear that you're supposed to use to start running ten man "raids," which in turn give you gear that you're supposed to use to run the 25-man versions, which drop gear for the 10-man raid that's the next step up in difficulty, which in turn provides gear for the 25-man version, onward and upward until you've cleared everything. For a new player, especially a casual one, injecting yourself into this path is problematic, especially if you're picking it up where I am and where most players are on the 25-man raids.
It might not be such a task for characters whose roles are strictly about dealing damage, but as a healer my primary function is to make sure nobody dies. No one wants to run any heroics with a healer who doesn't have the greatest gear, and normally this deficit is made up for by joining a guild that is interested in helping players run things incessantly until they have better gear and better experience.
Long winded paragraph aside, after sinking a small fortune in my server's auction house I bought a handful of "epic" items to make myself a bit more formidable off the bat. It would be no substitute for what I was supposed to pick up along the way but for the time being it was the easiest thing I could do. Geared a little less pathetically, I started soliciting groups to do the easier heroics so I could hopefully collect the gear I'd need to get started on the chain. At the start of this I met a guy running a guild who needed more healers. I explained my abysmal gear situation but he said the aim of the guild at the moment was to gear new members so they could actually run stuff. Sounded wonderful! He gave me a tentative invitation, asking me to run with them in a ten man raid they had planned in an hour, and I agreed even though I wasn't really sure if I had adequate equipment to manage it. It… did not go well. And when instances or raids don't go well, people get frustrated and the name calling and accusations start to fly. That the raid was largely comprised of people who, like myself, had just been conscripted an hour before didn't really help because there was no cohesion or coordination. People did what they wanted and the run suffered because of it. I stuck around for a couple days nevertheless, hoping that with other guild members available to do the easier heroics I could address the gear problem. This didn't work out all that great either as there were rarely enough people available to fill out the needed numbers, and I eventually started to feel pretty frustrated.
After a couple days, and more considerations as to whether or not it was really time to go play something else, I got invited into another guild run. These guys were a splinter group from a larger guild and had significantly better equipment and focus than the previous collection I was with, so things went much better and far less stressful. Again, they needed healers (that's part of the reason I created a priest, I'm always in demand, which was a far change from the level of unimportance I felt on my warlock character), and after explaining both the gear and existing guild issue, the guild leader promised that I wouldn't be leaving one group just to get myself into the same situation again. So, upon firing off a letter to the first GM, I /gquit and joined the new group. In the intervening time there's generally always been enough people around to do heroics, and I have managed to gather four pieces of gear to replace parts of my pathetic original equipment.
All of this is to lament the drastic change of focus in WoW once you hit the level cap. Despite Blizzard making such an effort to reduce the difficulty of instances and raids with the latest expansion, allowing such content to be seen by a significantly larger group of people, it is still prohibitively difficult to get into the current if you're not playing WoW like it's a second job. In the end you're just replacing the level grind with the equipment grind; when things are working well it's okay, but I really don't know how the top players on my server ever kept up enough interest in the game to get to that point.