Can there ever be a successful calendaring startup?

So Kiko got sold off, and Skobee slips silently beneath the sea DiCaprio style...   but we still hold out hope in the face of tractionless attempts at fixing what we perceive to be a real problem.   Calendaring and invitations, obviously going hand in hand, seem to work far from efficiently GigaLiz puts it perfectly...

"Every time we have to click through an Evite, we cringe. We can’t say we use Skobee, Renkoo, or even aggregator sites like EVDB’s Eventful, Zvents, and Upcoming
on a regular basis — that would require a mass migration by the people
we do stuff with. But we do hope that someone makes it easier and more
efficient to make social plans online."

Web 2.0 purists feel like Evite sucks, but you know what...  most mainstream tech users I know  have one of two opinions of Evite...   

It does the job...

... or they just don't like public RSVPs. 

I've never heard anyone on my softball team tell me that its unfortunate that Evite doesn't have more functionality.  In fact, the only thing I use that seems to work even better than Evite is a numbered list on the nextNY wiki...  which has even less functionality.   

The problem isn't client side...  in the invitation interaction itself, its server side and its on multiple levels.  Google Calendar didn't kill Kiko.  I don't know anyone that actively uses it.  In fact, I hardly know anyone who uses any calendar other than one their job forced them to... and less than half of the Outlook users I know put personal items on their work calendar.

Here are the nearly insurmountable hurdles anyone in this space needs to get over:

1)  Most importantly, most people just don't want a calendar.  It makes them feel too structured, under pressure, etc.  All these attempts in the "scheduling" space come from people like me who live by their calendar and whose life would be so much easier if everyone else did, too.  We keep thinking that, if there was only a good enough tool out there, we could get everyone using a calander, and that's just unrealistic.

2) Events drive calendar use, and only a minority of events are formatted to work with a calendar.  Think of the average family...  the biggest drivers of the family schedule--the kids' school and after school activities--are not in iCal, hCal, vCal, or any kind of call.  They're on a paper flyer or on a printed e-mail on the fridge.... or maybe written onto the fridge calendar.  Until schools get into Microformats, don't expect mainstream users to either.

3) You never know if the person you're inviting uses a calendar.  The beauty of Evite is that even if the other people never check the Evite again, it works for you when they click yes.  Try doing that to 100 people with an Outlook invite.  Half of the e-mail programs that open the message won't know what to do with it.  It was like when text messaging first took off here.  You didn't just randomly text everyone...  b/c you didn't know if they could get texts.  It took a critical mass of texting enabled phones for people to really get into texting here in the US, and reaching that critical mass took a long time. 

4) People don't want to let you know what they're doing.  What would really drive a lot of calendar usage is if you could negotiate for people's time based on levels of trust, open times in their calendar, etc.  For example, when I schedule a game of pool with my friend Brian, he's pretty much always going to accept an invite as long as he's free.  I should be "ok'd" to book a certain amount of pool in the empty spots in his schedule.  But, how can he expose his schedule to me w/o exposing it to the world, but also not come off like a complete loser if he doesn't happen to have anything booked yet for his Saturday night?   People share bits...  music, videos.. they don't like sharing information about how they spend their time...  b/c it makes them feel committed, locked in.

In the face of this behavior, what kind of scheduling service could ever be successful?