I realize people do a lot of custom stuff with WordPress, but it's been a long time since I had an upgrade not go smoothly and it's been a decent while since an upgrade broke a critical plugin as well.

I don't know if somehow the web just has a long memory of back when those things happened frequently or I'm just not the typical WP user but I have plenty of sites and it's not a big deal to keep them updated.

Annoying? Yes. But not that big of a deal. For someone like Scoble to call out WordPress despite the fact that he wasn't uptodate is just irresponsible (although unfortunately also quite typical of the drivel that's spewed by him on a regular basis).

Now, I don't think Matt handled it all that well getting pissed at rackspace but the point remains, if you keep things updated, you avoid a large percentage of the issues that hit WordPress users.

I don't mean to drone on, but I think it's time for Automattic to invest in WordPress security more heavily. I understand it's open source and always going to be under attack, but hiring someone with a devious mind to try and break things would seem like a great investment and would go a long way to assuring worried users that WP will remain safe and stable.