I stay pretty up to date on the WordPress updates. I just now updated all of my WordPress sites to version 2.5.
I am a Microsoft .Net guy, but WordPress is the best for blogs. WordPress is also the EASIEST thing to upgrade. You just copy the new files to your site and then go to http://SITENAME/wp-admin/upgrade.php
So if you haven’t upgraded to the newest version yet, please do so. I usually use Microsoft Live Writer to make posts but am testing out the online interface. Here’s a random photo of myself to test out how adding media works.
(EDIT: Adding Images still is a Pain in the ass. You can see by the image not actually getting added.)