I've been in a very critical mood lately. So far I have avoided criticizing those around me (you know, real people), which is a good thing. I can get pretty passionate about things. I've had three interactions with really bad software design recently.
myspace.com: Their layout and navigation is quite frustrating. I'm still not exactly sure what combination of links I have to click on to post a new "blog". Also, why are they the only site in the world that doesn't know that a blog is not a post... it's the whole thing, including every post.
Live.com: Signing up for a passport or live account or whatever they are calling it this week was a horrible experience. First rule of UI design, don't make your widgets move for no reason! In fact, there is no good reason, you're widgets shouldn't move after the page has finished loading.
Visio: The task was simple, addd some callouts to a diagram. The callouts were easy to add, but impossible to resize. Well it turns out that the designer of the callout object knew they were problematic, they went so far as to make the default text (before you replace it with your own) instructions on how to resize them... except the directions weren't helpful because they told you to grab a tab that wasn't there. So we dig through and try to find the property pages. Turns out the easiest way to adjust the width of the callout text box is to change THE HEIGHT! Somebody please explain this to me... or not, I'm not sure I want that kind of logic anywhere near my brain.