@DavidCoveny - It's not scary because of WordPress. WordPress is so easy to upgrade a monkey could do it (literally, it's just a matter of clicking a single button). The problem is that I'm EXTREMELY worried the software I'm integrating with is going to break. This is not a failing of WordPress, but a failing in the other software. However it doesn't make upgrading WordPress any less problematic. Last time I upgraded this particular site took me about three days to fix all the problems that occurred during the upgrade.