Seeing the Bears in 85 opens an old wound from my days as a Pats fan but this is an awesome post. Thanks Sarah!!

I hear you on paper calendars. I love them too but they don't work for a family that's getting busier every day. My kids are little, just 3 and 5, but we already have ballet, soccer, daycare, and school schedules, plus two parents working full-time outside the home. It's insane! I'm a calendar geek by marriage. My husband has spent the last few years working on the internet standards to make calendars work just like email. It's incredibly hard. I've had two big babies and I think this is probably harder than childbirth. (Shhh. Don't tell him I said that!) There's a group, CalConnect.org aka The Calendar and Scheduling Consortium, and they meet three times a year for five days at a time. They spend two of those days doing interoperability testing, seeing if the vendors' calendar servers can talk to one another. I'm amazed they don't all just sit in a room and bang their heads against the walls. That would be less painful than wrestling with calendaring. But progress is being made. CalDAV is the current standard and it's being adopted by most of the big players in this space. Whatever you choose, if it does CalDAV it will be easier if you change your mind later. Your data will be readable by something else. I am not in love with Google Calendar but it does everything you are asking for and it's free. And it speaks CalDAV. I'm using it at work, and though we have our own Apple OS X server at home (running mail, calendar, wiki, etc -- yes, we have a family wiki!) I have been able to make it all work together seamlessly. For me it's one tool in the toolbox, but it sounds like the right solution for you and your family.