I'd create a net share to hold the files, and simply point a virtual folder on each web instance to that place. Simple, and no sync issues at all, but this isn't always feasable.

If you have to maintain duplicate data sets, look into Unison, which is a bi-directional synchronization tool. I've had great results integrating it into Kix scripts, and it would be perfect for a situation like yours, where files exist in one place but need to be in two (or more) places. This can be fully automated. If files are MODIFIED, it gets a bit more tricky, but still possible with this tool.

Cool thing about Unison (besides being open-source) is that it works across platforms, and can ride over SSH tunnels to sync servers between different security zones.

Glenn
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Actually I am a Rocket Scientist! \:D