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I've been using Linux for so long now that I can't really say what would be the best way to go about learning it new. I also started with more of a Unix-type background rather than PC, so my mindset is different there too.
I think a good place to start is to actually perform an installation and/or play with a live disk. If you do an installation, you'll see details about how your disk is setup, etc.
When you've got something installed, you also have something to mess around with. It's at this point I'd look to have a goal in mind, e.g. like the Distro Astro stuff. Maybe work out how to connect up some gear like a camera, etc. You'll learn how to install software (usually via some package management system) and how to configure it.
As Linux is an operating system like Windows, you can do just about anything on it. With some of the distributions around these days, you could probably get by with as much administration knowledge as you currently have for Windows. I think the common stuff like wireless config, graphics cards, etc have GUIs these days, so it's not that difficult. There's also lots of sites out on the net to learn bits of linux or to find answers to problems.
So, after all this, the summary is: play with it, work towards a goal.
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