Howdy,
My mother is getting a Kindle 2 for xmas this year and I figured I would set her up with Calibre and load it up with a bunch of ebooks for her. Then I remembered that she is not very computer savy so I figured I should put together some very detailed instructions to help her along. I cleaned it up a bit more then uploaded it to a free web hosting site so she could get at it through the web.
http://madravings.xtreemhost.com/CalibreInst.htm
I figured since it was already online I might as well share the link in case anyone has suggestions or might find it useful. I am probably not the only person trying to share the Kindle joy with the technologically impaired.
Calibre is a very easy to use program, but I figured better over-explained than not.
Here is a link to the wiki version of the page:
https://wiki.mobileread.com/wiki/Add_...o_Kindle_Guide