I've searched elsewhere and couldn't find anything to answer this.

Has anyone else seen an issue with the way ActiveSync syncs files? I am specifically talking about the "Files" section...the one with the folder and the two blue arrows.

They will sync correctly the first time I Add... them, but not anytime after that even when I've disconnected the phone, rebooted my computer, etc. In order to get the latest version of the file on my Treo I have to Remove the file from the list and then add it again. Isn't this what ActiveSync is for?

Open ActiveSync/Right click on Files (if you are syncing any)/Select Settings. A window pops up called File Synchronization Settings and allows you to pick individual files from any folder on your computer to sync.