Tyler,
Please submit a support ticket and include the following information:
1) Your PDASyncLog.txt file located in C:\Program Files\Logbook Pro
2) Zip compress the following folder and include the zip file
C:\Program Files\palmOne\{Your Palm Username}\Backup
I'll try to reproduce your issue.
If you're syncing and you have enabled "AutoFill" to process in the top right section, try disabling that then resync by setting the date filter accordingly and see if this makes any difference.