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It is a bit clunky since you have to mount the share

To have it mount automaticially at log in, mount it normally, storing the login in the keychain. Then open System Preferences - Accounts - Login Items, and drag the share from the desktop to that window. Took me a bit to figure that one out, I used to use an apple script as a login item to do it.

Not sure of an easy way to do the VOB playback. I don't have enough storage to do VOB rips, so the few movies I have are H.264 transcoded.