First, yes, I agree (and I've talked about before) the name "WWDC" is an impediment. Having said that, and still saying that, the truth is, for any sysadmin, if you can only go to a single Mac-based conference, this is the one.
The obvious reason is the content at the event. The first session is (of course) the keynote, and the preview of the next major release of Mac OS X, Mac OS X 10.5, aka "Leopard".
While anyone with the right Apple Developer Connection membership will get a copy of Leopard, getting a chance to spend a week asking questions on the new OS to the engineers who wrote it is, literally, priceless.
Every network is unique, and every sysadmin's needs just as unique. Getting a chance to talk to your peers and Apple engineers at the same time, either in sessions or in person out in the hallway is an opportunity of astounding value. There's almost no way that email, or mailing lists, or forums can recreate the kinds of knowledge and information you get at the WWDC, because the conference creates a kind of feedback loop, where someone else's question or statement is going to spark a question that you might not think of.
The spontaneity that the conference allows for isn't something you're going to easily duplicate anywhere else. There's nothing you can get out of email like having a laptop running Leopard in front of Apple people and peers showing them what you're talking about.
Outside of the keynote, by the end of the first day, you have the Mac OS X State of the Union, the IT State of the Union, and the Mac OS X Server Overview. You want to know where Apple is going in those three areas, well, there you go. 4.5 hours of live info with Q&As. Again, situations you cannot recreate via email and mailing lists.
But it's more than that. Java, Active Directory integration, Spotlight, .Mac, QuickTime Streaming, Network file systems, Core Data, on and on. Day after day of immediately useful information, and that doesn't include the fun of discovering what the "Session to be announced" spaces cover.
Take shots from the firing line
I guarantee that at some point, you're going to have to make "the horrible choice" between two sessions that are absolutely perfect for you. I already see my first one. It's on Friday morning, at 9 a.m. Sessions 526 and 527. I'm absolutely positive there will be more. There always are.
Then of course there's the feedback forums. They tend to look like a firing line, only the audience has the bullets. But again, if you have a serious concern about Mac OS X Server that you want most of the Server management team to hear, well, they'll all be in the room, and you'll have access to a microphone. Fire when ready, Capt. Crane.
If there are any hardware announcements, (and there usually are), then you'll get the first chance to play with the new toys. Not in a Macworld Expo madhouse with 30,000+ people to contend with.
The Labs, which run late into the night on Wednesday will give you a chance to beat on the new toys. Last year, who got to play with Mac OS X on Intel first? WWDC attendees. Heck, who got to work with iSights first? WWDC attendees. Who's going to get to play with the new OS and possible hardware, (Considering the shipping status of the Core 2 Duos, and the fact that they're now 64-bit, and the vector processing bus size mismatch has been fixed, I'd be pretty shocked if we didn't at least see some desktops. Personally, I'd love a laptop refresh, as I'm holding off on a new rig at work until the WWDC keynote. Normally, I'd just get it, but less than a month before a WWDC? Are you kidding me?)
Face it, when you're talking about the core technologies that are going to dominate Your Mac Life (sorry Shawn) for the next year or so, the WWDC attendees not only get to work with them first, but get to have the source of those technologies right there in the room with them as they work with them. You can't even come close to duplicating that kind of knowledge transfer.
Yes, it's expensive, and yes, it's an odd name for a conference that most definitely is not "just" a developer conference, but I've found that the worst direct ROI I've ever had was something like 90 days.
In 2004, I got enough information that my ROI was about a month, and the value from the 2004 WWDC ended up being more than the cost of the 2005 WWDC and most of the 2006 one. I've never gone to one and wondered why I bothered. Mostly, I wish they could be just a little longer.
I've been going regularly since 1999, which still makes me a newbie at the WWDC game. It's always been worth the effort, usually 10 minutes into the keynote. The one I missed, I kicked myself for the rest of the year for not going.
I'm not making that mistake again. Look at the session listings on Apple's WWDC site. You'll have your justification for the expense within 30 minutes. Oh, and since my next column will be published on the Friday of the WWDC, I'll give you three guesses as to what I'll be talking about, and the first two don't count.