I have no problem mentioning what I voted for, which was 'Yes, with limitations'.
As you mentioned, guilds/free companies are nice to have. It helps give members autonomy and allows them to feel like they are fleshing out the world. However, I can see where your worry comes in with... the issues that you mentioned. You brought up some good points. While I don't know if any of these will be the correction answer (spoiler: we'll never know!), I do believe this might help you with some of your decision.
What if a character is part of a Guild but they don't want to be the leader? Would they need to be responsible for that entire Guild?
That begs the question if you are planning on incorporating player-made guilds into your plot or not. I'd personally err on the side of not allowing them in any site-wide plot and keep core staff-run guilds as the bread and butter for those events.
Should there be requirements so people aren't just making willy-nilly Guilds with one or two people in them?
Yes. A thousand times, yes. Even in games, there are normally requirements for making guilds. Since you mentioned a shop in your original post, you could use that as part of the requirements. I'd also factor in post count to act as an activity gauge. While someone could potentially have reach the required quickly, the post count should help alleviate some issues. (I'd probably also limit this to IC posts and no OOC posts as well.)
What about inclusive-ness and if someone restricts certain people from joining?
There's always going to be some sort of clique mentality forming. So, this would be a knock against not including player-based guilds at all. If someone is rejected based on characters not working, that's one thing. But if it's the player themselves, that would need to have staff get involved.
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