I'm using VPNC on an N800. When the boss saw me with an SSH session over VPNC to a 'secure' server while having lunch at the local pub he had me order two N800's for his family.

I'm not sure if you said the remote machine is Windoze or *nix but something like rsync, sftp, etc should be able to be scripted on the N to move the files automagically.