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I've been apart of two reroll raiding experiments. One failed drastically and the other is currently working well. A major ingredient in getting over the hump, in my experience, has been doing ZA almost as soon as you finish killing Prince. The drops in there are relevant into T6 content and the fights are more coordination and group comp than gear.
Both guilds I've been in formed around january and were basically complete rerolls. 3/4 5/6 1/5 2/9 in a matter of months. If we wanted to we could skip Vashj/Kael and prolly be much further in Hyjal and BT but we aren't for a number of reasons.
Recruiting, as usual, and finding a solid base of players is the hardest part. Have to find the right situation. Our guild is a combination of a bunch of transfers who were looking for the same thing and close friends who have been around. Not sure how far we'll get before WotLK.
In my old guild I was the recruitment officer and basically spent 80% of my time fishing for people on the server and in the guild recruitment forums. It was an RP server with no BT guilds so there were ZERO ripe raiders to be had. I was barely able to scrape together 25. Can't imagine what it'd be like if we needed 40 regulars. It failed because the raid leader didn't know what he was doing and was an egotistical maniac.
Even if you have a core (let's say a tank/RL, geared healers, and a really really good dps to set the bar) it doesn't really work unless A) you have 20 other solid people around you or B) you want to spend the time to teach people how to play and push the edge of content.
In Summary: Learn how and who to recruit. Set a pace and try to meet it. Get lucky.
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