Hi rcstribe,
Recommend? Backup. Backup. Backup. 🙂
I’d recommend copying your site to a second location, whether in a subdomain on your server or a local install, and giving it a go there. I’d try updating WordPress first, which usually goes smoothly. If that works, I’d backup again. Then try updating the Events plugin(s). It’s a fairly substantial change between 2.11 and 3.3. If you want to be uber cautious you could start with the 3.0 release and then jump to 3.3, but that’s uber cautious.
– Julie