Found the problem/solution, Dave.
After creating my backups, I booted to the main drive and did nothing. Then I booted to the external backup I just created and did nothing. Started up to the other external and did a Smart Copy from the 2nd external to the main drive. Out of 144,599 files examined, 187 were copied to the main drive. Upon booting to the main drive, Word and Entourage were once again broken.
Since I hadn't even launched either app on the external backup, it had to be something else. So I went into Onyx and removed the swap file along with every single cache and system log file. Restarted, and Word and Entourage were happy again.
So while I don't know why these two apps would be so sensitive to the state of a cache file, they apparently are. I wasn't about to start over and remove them one at a time to get the exact cache file. The shotgun approach works just fine for me.
Thanks!