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Have you tried Group Calendar?
This is best in that you can schedule certain events and they can check wether or not they choose to attend. Unfortunately, you wmight want to assign a guild officer to moderate these to keep people honest. If you are requiring them to bring specific items to the guild then, it should be easy to track as they can enter them into the guild bank. Group Calendar is also good for scheduling meetings, instances, raids, etc.
I have made it a standard in my guild. Once someone joins, they will be an initiate until they have Teamspeak (to be able to talk and hear), Group Calendar and be at least level 30.
That's all I can think of that might be of value. The only other thing I can think of is maybe contacting and paying a developer of add ons to make a specific mod for you. If you do this - I would certainly raise more than an eyebrow :) !!!
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