Well, to get the ball rolling, heres where I'd recommend starting out:

First off, I'd get a windows-user-friendly Linux distribution. I hear good things about Suse with its Yast configuration thingamajigger. However, I understand that the free version of Suse isn't particularly easy to get your hands on, meaning you could/should go buy a retail box from your local computer store. Installation should be a breeze. My distribution of choice happens to be Debian, but I don't recommend it for a newbie.

Suse uses KDE by default as the user interface and most other distros have KDE as default or as an easily selectable option. I recommend KDE as it should be mostly familiar-feeling for a windows user. Spend some time familiarizing yourself with things. Find a text editor you like (kwrite perhaps? similar to Textpad)... look at the general structure of the filesystem (/etc, /usr, /home)... read the primers or tutorials that come with your distribution's documentation.

When you feel more comfortable, tackle getting a web server configured. There are some things that can help ease this task such as Webmin, a web-based administration tool for many things Linux.

Despite the hype, maintaining a Linux box honestly isn't as easy as a Windows box. Once you are familiar and comfortable with it all, it starts to make sense, however.

Where to get help? I'd check google for linux primers for windows users, I'm certain you'll find plenty. For specific questions on how to use something, I usually start by skimming the manpage of the program I have a question about. Then, check I check the web site of the application in question for mailing lists, FAQs, HOWTOs. Finally, I scour google and google groups. (not necessarily always in that order)