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How hard to snap on a disorganized frontman

So as I type, I've got two messages in with the frontman of one of my bands, which has good potential to step up to a national level next year (like my other band). One message is to pick dates to meet with two producers, both of which are eager to meet, the other is to ask him to move a gig he booked the same night I've already booked (date's a month away and I emailed him about it a month ago). He's currently chatting on Facebook, no response to either of my rather urgent and time-sensitive inquiries.

He's 20, but mature for his age, not overly sensitive, drug-free, has an iPhone, but won't spend the five minutes to set up his calendar and synch it with ours. He lives an hour away or else I'd pay him a visit.

I'm curious to hear what others would do in my place. Part of me wants to be passive aggressive, and when the date arrives just say "I booked mine first, it's your mistake, you fix it" but obviously that's not especially professional.

The reason this really pisses me off is because I know most venues book the bands that are easiest to deal with most. As with most industries, people who can provide answers the fastest get the most calls. Bands whose members all have smartphones with data plans and calenders kept up to date get more gigs. It's no more work than a paper scheduler, you can share calendars to instantly see when everyone's available, and the additional gigs pay your whole phone bill easily. Why would anyone call a band that takes a week to confirm when they can get an answer from another good enough band right away?
 
I totally understand that frustration. I have some lazy band members who don't book gigs, then complain that we don't have enough gigs, and then take several days to get back to me when I send them dates to books. We have lost a few gigs this way. In this day and age and the technology that is readily available, there really isn't a good excuse for not communicating.
 
Man, you say you have potential to step up to the national level and yet you're having to deal with this sort of thing? Might need to have a face to face sit down with him, because if he's this neglectful I highly doubt you're going to make it to that level.
 
He's 20, but mature for his age, not overly sensitive, drug-free, has an iPhone, but won't spend the five minutes to set up his calendar and synch it with ours. He lives an hour away or else I'd pay him a visit.

First tell us about the mature part because I'm not seeing it. Second, you think you have the potential to be a national act but its not worth the effort to drive an hour to talk to him??? Either the potential isn't really there or you aren't too motivated yourself.
 
Apparently you need to take charge here. That means going into problem solving mode.

Regarding the date conflicts? Take charge. If your date was booked first, make that the priority. Present the singer and the rest of the band with alternate dates to move the conflicting date, and get settled on those alternates ASAP. Then approach the conflict venue with those alternate dates and apologize for the confusion.

After that? I'd say it's probably time for a band meeting where booking activity gets consolidated. Booking conflicts are an easy way to get a bad rep with venues.
 
This kid is NOT "mature".

Mature individuals know how to prioritize, and they take personal responsibility ESPECIALLY when they are tasked with making decisions that affect the lives of others. It sounds like this frontman (he is most certainly not a "bandleader") is badly lacking on both of those attributes.

To the OP, good luck. I'm sorry you're in this situation cause it must be frustrating as hell.