Don't I feel like an idiot. I was in the process of backing up all my files as John Clark suggested and I noticed something in the directory. It basically looked like this:
Originally Posted by BlackBerry Media Manager
My BlackBerry/Media Card
Apparently I had all the files stored in the Images/Videos folder and not the respective BlackBerry folder. Doh!
Sorry for wasting everyone's time, but thanks for the help!
I'm new to the BlackBerry cult and hope to learn a lot and eventually contribute back. Thanks guys!