Without naming names, I'm going to hurl a brick in the general direction of any or all Web 2.0 startups whose purpose is to let you schedule an appointment with someone else. This is not going to drain the swamp! In fact, quite the opposite.
Why? Because each one of those new services requires you to create a new account on some Web site somewhere, and each of these accounts has to be kept in sync with your own calendar somehow. Many people will simply not bother, and instead will have a new flood of reminder emails landing in their inboxes. The average person has, maybe, two or three online calendars today. When we have all these new services for your kid's teacher/mechanic/doctor/yoga instructor etc. etc. then the average person may have six or seven online calendars. I think that's a problem.
(I'm not even counting another whole class of Web 2.0 services that allow you or someone else to send you reminders, whether it's to do something, or take medicine, or pay taxes, move your car, or remember something else. These services also emit emails and text messages which probably don't end up displaying on your calendar. Maybe that's fine, but if like me you'd like it all to appear on your calendar, maybe it's not fine.)
Now, do I have a solution? I'm not sure. I'd like to see federation of these calendars, that's for sure. Something like Open ID for calendars. That way, these online calendars could all confer with each other without requiring customers to perform lots of syncs or manual import/exports. I'm not sure what's on the drawing board that would allow this, and I haven't been super impressed with Open ID both for its features and its adoption curve, so I'm afraid things are going to get a lot worse before they get better. And it's been hard enough to get calendars to simply publish and subscribe to each other, so what I'm asking for may be another exponential engineering effort.