I was in a pretty big but still family type guild starting around Luclin. When PoP came out and the majority of us had at least 1 character at 65 we started raiding all the content in Kunark, Velious and Luclin that we could handle, I think we managed most of them (you can probably figure out which ones we skipped.)
From the gear and skill we gained on those we started slowly working our way through tier 1 and then tier 2. LoY was already out by the time most of us were flagged for Tier 3. And things kind of fell apart at that point with people moving on to raiding guilds and others concentrating on getting LoY gear (because they gave up hope on us getting to the end game.
I stopped playing for a month or 2 and came back when GoD came out for a little bit at which point the guild had lost all sense of direction and was tagging along with other guilds for flags and newer content. At that point I realized that I would be playing catch up forever with "necessary gear", "necessary flags" and "necessary AA's and I just quit for good.
I'm kind of hoping that I can make it to 50 this time before Kunark comes out but I'm married now and just don't have the time I did back then. I just hope I'll find a guild that's on the same time line as me because the only raid mob I have ever seen from the old world is Vox a few times. Yeah, I know it's sad.
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