is even simple automation possible

FCSvr is highly scriptable, and if you want more automation than you already have (as opposed to encoding a proxy by hand and then manually uploading it to an FTP server), you'll need to look at what parts of your workflow can organically trigger an automation instead of requiring specific input.

Yes, a manual "automation" is requiring those steps. I've tried to add a tickbox in the list view or in the thumbnail view, or in the first page after double click (Asset metadata), but I couldn't do it.

To organically fit your "automation" in a workflow could be done at the time of ingestion (assuming you'd already know from which assets you'd want to send the proxy to an FTP).

Create an ingest-and-send-proxy-to-ftp watch folder and create a watcher followed by a subscription to get your proxy to the FTP fully automated.

You could also consider some scripting outside of Final Cut Server using the XML-write / XML-read principle. At the time of ingestion you could have FCS to automatically write an xml. Whenever you need the proxy to be sent to the FTP, your external script could send a read-xml to FCS with a trigger to upload the proxy to FTP.

What I'd like to know from you is how did you get: "Automations under Metadata" and "Send proxy to FTP"?

Is "Automations" a metadata group custom made by your administrator? and is "Send proxy to FTP" one of the automations created by the administrator?

And finally: the action "Send Proxy to FTP", how is it done? Is this done by a script which is getting the proxy file and duplicating this to the FTP, or is it done by copying the file to FTP with the transcode setting for the proxy file (i.e. recreating rather than duplicating)?

Thanks, Henk