I have huge issues getting people to sign up for our raids. I'm guessing this is due to the tedium of it?

Is it possible to add a quick sign up link for each event on the big calendar? No late or notes and always for their main character. Just a little (sign up) after the event name that they can click on and without even doing a page refresh will change to [Signed up] and then they can click on another until they have done the entire month from one screen in a matter of seconds.

Example

20th
2:00pm - Zul'Aman (signup)
10:00pm - Karazhan (signup)

Interesting idea. I think I can swing something like that.

Would be nice if you could. It would great increase the speed and willingness to get them to do it. Also, less strain on your web server.

Perhaps allow people to define a character's default role somewhere in the profile, as well, so using this option on, say, a Druid like myself, on a site that uses role-based signups wouldn't pigeonhole you into a random role.

I like this idea. I also thought about a "Mass Signup" option or something like that. You click the link and any future raid that's on the calendar would be listed. It could have check boxes for attending and not attending. And it could also have drop-down boxes for roles. Heck it could even have a field for notes and what-not. It would all just be listed by date/time so you could run down the list quickly. Maybe have separators between dates so people could tell if there's multiple raids scheduled for 1 day. I would also recommend the dates also show the day of the week as some people can't make it certain days, etc. Haven't thought it all the way through, but food for thought.

Here's what we're gonna do for my guild and perhaps this idea can be propagated into the website structure. We have 3 Kara groups Alpha, Bravo, and Charlie and we run 25 mans with more or less the same bunch each week in Gruul's, etc.. Each week Tuesday 11am to coincide with the reset there is a scheduled event there for each Kara group and the Generic 25 Man team. That is what is refered to when building each raid and when asking who is saved where.
As far as changing the website structure, it would be nice to have the signups divorced from scheduled events and also to give the ability to officers to assign people (sign them up on their behalf) to a signup, so TEAM based signups rather that TIME based signups.