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Step 1
Keep up on Apple rumor blogs. The is hands down the best method to figure out what Apple will be doing next. There has never been an Apple product release that wasn't talked about on a rumor site before release. Whether it's Macrumors, TUAW, or even a more general gadget blog like Engadget you're guaranteed to get a heads up there first. The downside here is that some of these sites are littered with impossible rumors. Sometimes even the most credibile of sources will report a rumor that just isn't going to come true. The more you read from these sources the better you'll get at picking the good rumors from the bad ones.
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Step 2
Apple typically holds their World Wide Developer Conference, otherwise known as WWDC, in the beginning of June. There is always some kind of big news item that comes out of WWDC. It's usually software based, but can involve hardware sometimes as well.
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Step 3
The yearly back to school promotion usually ends in September. This promotion isn't just a sales tactic for Apple - it also clears out their old inventory! Without fail, Apple updates their notebooks once before back to school (usually April or May) and once after (October or November). Given that the last few back to school sales have involved iPod promotions, Apple often puts out a new and/or improved line of iPods in the last few months of the year as well.
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Step 4
Keep track of Apple's product lifecycles. The Macrumors' Buyer's Guide is great for this. It'll show you a list of dates for each new release of a given product and how many days (on average) it's been since release. It will even go so far as to tell you when you should and shouldn't buy a product based on whether they expect new updates soon. Keep in mind that this is still little more than an educated guess. At the time of writing the iPhone has doubled the usual amount of time it goes before a new update.
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Step 5
Watch from the yellow post-it. It's become an icon of the Mac community. Every time a new Apple product comes out, they briefly close the online store for "maintenance". When the store goes back online, there's new Apple products! Note that this doesn't mean every store outage calls for new products, only that new products call for a last minute outage.
