Silent updates?
The tricky part about automation tools is that it sometimes has an update for the updater, which you need to acknowledge. Then the update itself is very different in how long it takes and a dedicated server would have to be down the maximum time any update would take (like 3 hours). And DCS can’t be running as long the updater is running. I guess if you’d start notepad first (to handle any stray keypress) and then press Enter after starting the updater it will either acknowledge a new updater or start updating, then waiting a few minutes for updater to finish downloading and pressing enter again will either start the update or switch to html download, then wait 3 hours and press enter again for acknowledging the update has finished (which should close the updater and allow DCS to start). Then Alt-F4 and N to close Notepad.
Edit: do you need to acknowledge the switch to HTML download? If so the script needs to run for 6 hours.