I upgraded the site to WordPress 2.3 this evening. I’ve been putting off updates because, quite frankly, it scared the hell out of me. One of the reasons I picked Yahoo for my hosting was, besides being big enough I felt I could trust it to just work, that it had a auto-installer for WordPress. At the time I was under the impression that Yahoo would also keep the installation updated. But that doesn’t seem to be the case.
I recently found out about a plugin which does the WordPress update for you. Which, in my opinion, should be built into future versions of WordPress. In fact, I think it would be a good idea of the plugin’s could be updated from within WordPress system as well.
Everything worked well but I got some nasty looking error messages when it tried to update the database. Everything works tho, so I’m happy.
Now, the plan is to get a new theme for the site. The newer versions of WordPress support a dynamic sidebar and it’s a lot easier to change around. But the theme has to support it. I should be able to edit the current one but that’s a little too much effort for me. 
I’ve searched through 20 pages of theme’s and these are the ones I like so far:
They all follow the same sort of look, which is also similar to the current theme. I’d like to customize the theme to make it “my own”, but I pretty much just want to change the picture files. I’ll have to test these out when I get some time.
