There's no way how to watch for changes in remote directory apart from repeatedly re-reading it in regular intervals. In upcoming versions WinSCP will allow to synchronize the directorins using command-line. Together with Windows scheduler you will be able to set up this.

My company uses samba as the main file server. I would like to backup samba (remote) on my home machine. Would it be possible to add the feature "to keep the local directory up to date".