In case anyone else has this problem, I found the problem, so hopefully this helps you out.
The problem? Creating a custom logbook format and not loading properly. My issue was that even if I just selected "Create a custom format?" and used all the defaults, it still wouldn't load. There's an actual bug in the software, so the fix is to go to:
First, backup your logbook, because you're about to delete the files.
Next, click, Start...run....type REGEDIT to open up the registry editor.
-Expand HKEY_CURRENT_USER
-Expand Software
-Expand VB and VBA Program Settings
-Find any entries on the left with "Logbook Pro" in the text, right-click and delete each one
-Close the registry editor
-Reopen logbook pro and reload your backup file.
Everything worked normally after clearing the registry.