"Most people shouldn’t be running their own blogging software. Services like Tumblr, Posterous and Blogger are excellent and free. WordPress.com, the hosted version of WordPress, gives you 90% of the benefits with none of the hassle."
When I first started with a website I used Blogger as a backend to my site. I've also used static generation with Nanoblogger. And even had a bash at my own built blog in Rails. I've never used Wordpress, but agree with the sentiments that nowadays it makes much more sense to let someone else do the hardwork. For my latest incarnation I chose Tumblr, which is excellent to use, BUT has one major flaw: No proper backup facility. Sure there are tools and applications, but nothing integrated. So in that respect you are almost living dangerously as hosting Wordpress yourself - you could still lose all your content. I hope that Tumblr fix this someday soon.