For our first official meetup, we'll be discussing the differences between wordpress.com (where your blog is hosted by Wordpress) and wordpress.org (where you install WordPress on your own server). We'll also be doing a live site installation on a hosted server, from beginning to end, so that users can see the new installation.
Because interest so far is coming primarily from the end-user part of the spectrum, we'll be focusing on this entry-level topic. However, designers/developers and advanced users are, of course, quite welcome to attend and offer their input.
I (John) will be hosting and presenting this talk. I'm an intermediate level end-user myself, so you're not getting expert advice, and I may not be able to answer more complex questions. However, I've done many, many site installations and am very comfortable with the whole process.