Several of my friends have started getting blogs on WordPress.com, the fully-hosted version of the blog software I use on my own site. Most of them moved over from LiveJournal or Blogspot, and most of them are not techie types, or at least not web heads, so a fully hosted solution is perfect for them. I briefly thought about joining them, as I’m a lot less tweak-oriented than I used to be, and besides, things are a little out of hand organization-wise over here (though most of that is transparent to the reader).
And then I realized: I like flexibility. If you use the fully hosted version of WordPress, you are limited to the designs and plugins they choose for you – and there are SO many more out there than what they offer! Sure, things might be messy on the admin side of things over here, but it’s a mess I made, as I tinkered and tweaked just how I wanted.
Everything that WordPress.com has made easy – upgrades, new plugins, new themes – is now part of the base WordPress program. (I used to get paid to upgrade WordPress for friends, before they became a one-click process!) It couldn’t be easier to run your own WordPress installation today, and have super flexibility. Most web hosts even offer it as a one-click installation in the first place! You do need your own domain, and not everybody wants that, because it costs money. But if you have one, you don’t have to be tied down to what WordPress.com offers you.
A little bit of my own blogging/web history. My first webpage was a school project in 1996, hosted on Geocities, back before they had subsections under the neighborhoods. Then in college in 1997, I had www.geocities.com/CollegePark/Union/1234, where 1234 was the number of the house where I grew up. In 1998, I moved briefly to Tripod, and then to Chickpages. In 1999, I bought amanita.net, and I’m still here. 
I blogged a little without software back in the day, and then in 2001 I started at LiveJournal. I switched to self-hosted Movable Type in 2002, and to self-hosted WordPress in 2004. I have been hosted with Virtualave, Blogomania, and Dreamhost. My webpage is my favorite hobby, though I haven’t done much with it since I went back to school in 2007…but after I graduate I will probably tidy things up and make everything perfect!
I miss having my own domain and the self-hosted WordPress, but I just couldn’t justify spending the money when I really didn’t have it, and when so few people actually visited. I’ve long used your site for inspiration.
You have SO MUCH control with WordPress. I use it on my site and I can say it’s 10000% better than wordpress.com. The most beautiful thing is monetization, you can choose if you want to put a particular ad network on self-hosted WordPress while you’re quite limited on wordpress.com