So the one (and only) stress test that I was able to perform shined light upon a couple of minor things that could easily become major headaches. Therefore I haven't done the software upgrade. The host is working with my schedule and there is no immediate pressure to get it done. So in all likelihood it won't happen until after this semester.
The main reasons for doing the software upgrade are: server software will be upgraded eventually and won't officially support this version of the forum software, the upgraded server (and forum) software will fix known security holes, forums should be a bit faster, easier to customize, and more robust.
It's not a huge change as far as the user experience goes, just minor visual changes with some moderate functional changes that will all be explained once it's all said and done :)