I LOVE guild leading and organizing events and finding reasons to bring characters/people together. But I agree, leading ONE guild is hard enough, leading more than one is nearly impossible without dedicating your life to the game, and IS impossible without some good guild officers to run things for you while you handle other business.
My first guild actually went pretty well (all things considered) on a Normal server. I was focused on using only IRL friends at first, and then branched out to people just looking for a safe place to learn the different aspects of the game. It was called The Motley Conflux, to emphasize that even though we all had different reasons for playing, we were bound together. When I moved to Cenarion Circle, I reflected on TMC and thought of it as a school. I wanted to bring that idea to the server, like a training guild that would teach folks whatever they wanted to learn about the game, from battle pets, to PvP, to roleplaying, dungeons, mat farming, toy collecting, etc. The idea was shot down as “dumb,” because “people here already know how to play, no one wants to roleplay being a noob.”
Eventually I grew attached to Troubadour Night, and I thought it would be cool to do group performances. When the opportunity presented itself, my group of friends banded together to form the Bards of the Lion, a guild originally designed to gather stories from fellow adventurers and put on plays to re-enact moments of the server’s history. The guild’s evolved since then to accommodate interests of the server, but the mantra still exists: Boost morale of the people, and preserve the lessons of hard-fought history.
On the antithesis of that, I did want to make an evil guild organization, but my last couple attempts have failed due to the fact that I already had Bards, and in order for a guild to succeed, you have to maintain a constant presence, so your main has to be in the guild. Balancing Bards and Villain stuff was too much. Their outward appearance would be “hardcore war training”, as heroes are only made strong by the conflicts they face. Inward appearance of course would be “it’s just fun to be evil, let’s go stir some chaos and see if we can take over the world!”