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Let's not all forget that, due to FCC filing deadlines, Apple had to announce the iPhone way ahead of its release last year. As I understand, FCC filings for product updates demand less time and can also be cloaked to a point. So, my guess (and that's all it is) is:
Apple announces the new iPhone as early as this week, and starts taking pre-orders. That should partially take care of revenue during this time of no supply of the current model (some people just aren't up for pre-ordering something they can't put their hands on, myself included). Shipments would start in June, post software 2.0 release and in time to justify the AT&T vacation ban, since it would not be available in AT&T stores until then.
Would that rob Apple of a stage on WWDC? Somehow. We may be getting to the point where an FCC leak might be likely to spoil any sort of announcement by Apple, so they'd take a surprise online announcement of the upcoming iPhone (pre-order now), and use WWDC to put the hype into overload with the new software demo, new applications and immediate availability, besides giving the specialized media time to review the product and build even more hype ahead of its release.
As for how a new product would fit into this, I think that's a different issue altogether. None of this discussion precludes Apple from announcing a new product in the old "one last thing" tradition of surprising us, which, as we all know, the new iPhone wouldn't fulfill, since we all expect it.
And as for the shareholders argument, I agree it would be troubling to go an entire month to a month-and-a-half without revenue from one of your main product lines. But overproducing a product you're about to EOL and end up with tens of thousands of expensive products in stock you can't get rid of is equally troubling for shareholders. In trying to strike that perfect balance, they might have miscalculated. Because I believe Apple is smarter than that, I give credence to the rumor that at least an announcement might come before WWDC.
To be safe, even thought I've been waiting for 3G since the iPhone was announced, let alone released, and sitting on enough Apple Store gift cards to get one for about 6 months, whatever they announce earlier than June won't be getting my order until I see what's out of WWDC. If I've waited this long...