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(More braindumping - not quite at the article level yet! =) )
When I plan presentations, I always start by coming up with the key message based on the objectives and the expected audience. The key message needs to be something I can explain in at most 30 seconds, and it needs to answer the audience's question: "What's in it for me?" The key message also needs to give people a way to act on that message. (Yes, even FYI presentations.) If I can't explain what I want to say in 30 seconds, I mindmap and brainstorm and turn things over until I can.
There's no point in working on the rest of the presentation until you know what you want people to take away. If you can't say what you want to say in 30 seconds, think about the topic until you understand it well enough to say it in 30 seconds. When you figure out what your 30-second pitch is, you can use that as your abstract and you can use it in networking conversations at the conference/event/wherever. Very useful.
After I determine the key message, I pick three or so supporting points. This is also where I try to find a clever navigational structure or mnemonic to help me remember my points and to help the audience remember my points. Alliteration and acronyms are my favorite tools, but I occasionally come across a good metaphor, too. If I can't find anything that fits, I try to at least get the rhythm of the words to sound right. (No, I haven't given a presentation in iambic pentameter yet - but I'm tempted to! ;) ). A thesaurus helps me find synonyms that fit, and a dictionary (I usually use a kid's dictionary) helps me spark the creative process with random associations and browsing. (Flip it open to a random page, pick a random word, and see if that's useful.)
Resist the temptation to cram lots of points into your presentation. Find the minimum that you need to support your key message, then get those across clearly.
So there's the 30-second pitch, the supporting points can be summarized over three minutes or so, and you can wrap it up and explain the next actions in another minute. When the presentation works as a 5-minute talk, it's time to flesh it out to a 15-minute to 30-minute talk. You can do that by adding stories to the supporting points, keeping the key message in mind. Stories can take varying levels of detail, so they're pretty flexible.
To take a talk from the 30-minute mark to the 60-minute mark, add more interaction and deeper stories. Good interaction tends to require a longer presentation slot because you need some time for people to shift into discussion mode (and you have to be comfortable with silences), and you don't want to cut discussions off too early. If you're doing interaction, don't make question-and-answer the end of your presentation. Move question-and-answer into your presentation, then take advantage of the opportunity to summarize both your presentation and the discussion with a strong ending, emphasizing the next steps.
Longer timeslots such as 1.5 hours or 4 hours or even days need to be broken up with more interaction and variety. From my university classes (both attending and teaching), I learned that attention tends to flag after about 20 minutes. Mix things up and give people time to process the information. (And to stretch!) Resist the temptation to structure your presentation as one loooong presentation. Break your presentation up into more presentations, because it's important for people to have review and closure.
In this approach, you're building up from the core message. As long as you can make that point, you don't have to worry about leaving material out. If you don't overload your slides, you can quietly trim material in order to accommodate a particularly good discussion (or a long rant about something else) and people won't feel cheated. =) If you find out that you have to talk for longer than expected (say, the next speaker is having technical difficulties), then add more detail or more stories or more interaction. If you find out that you have to talk for shorter than expected (say, the previous speaker had technical difficulties ;) ), focus on the key message and the supporting points.
Try it out for your next presentation. Start with your 30-second pitch, then build on it. When you get used to adjusting the timing on the fly, you'll always be able to end on time.