I get this question all the time …should I upgrade to this new latest and greatest version? Normally, I would say “Yes, you should be running the latest version of wordpress to protect yourself from the spammers out there in the world”.

However, this time I am saying:
“Maybe”

I run about 20 blogs and I consider myself an expert with wordpress. Currently, I have upgraded about half of my blog stash and I am leaving the balance at version 2.3.3 (which is safe from any security holes) …if you are running a version lower that 2.3.3 …HIRE ME QUICK!!! …seriously….There are some crazy people who could do mean things to your blog.

All of my 2.5 upgrades have NOT gone smoothly. Plugins don’t often work. …and many plugins will need to be upgraded. So, if you are going to attempt it…don’t even think about starting the project when you are the least bit tired and cranky.