Here’s an email I sent a friend this weekend. Not sure why I’m feeling like reproducing it here, but I do.
You asked about getting into blogging.
As far as front end goes, I recommend blogspot over the others. Seems relatively straightforward and reliable. And it doesn’t come with a “rep” like livejournal (though livejournal is perfectly fine as a system and the rep is undeserved).
You should think of it a pseudonymous instead of anonymous, since you’ll be writing about real people including yourself. Come up with consistent names for your “characters” that are easy for you to remember (e.g., change all first names by one letter — Jon becomes Ken, for instance, though I would never want to be a Ken).
You also need to think about how anonymous you want to be. For instance, if you want your friends to read it, that’s relatively anonymous (see, e.g., http://gonecompletelyferal.blogspot.com/ for an example) but you will need to avoid self incrimination because unless you swear each one to secrecy, it could eventually come out that “Blog Y” is really “XXXX’s blog.” Still, you have plausible deniability.
The other option is to go completely “dark” and just have one or two confidantes or none at all. In this case, your set of readers will come as you comment on other blogs and link back to your own (people will follow).
You need to also think about tone and personality. A blog, like any other autobiographical writing, basically creates you as a “character.” Since my blog is under my own name, my character is perhaps more consistently positive about all matters than I might be in person. I also can’t write about certain really funny things that happen while I’m at work because they involve others whom I may not wish to discuss in public.
Finally, either way, you may want to do a short test run before going public. See if you like it. Like restaurants, most new blogs fail within a few months.
That’s all I can think of for now.