As a step towards automated upgrade of the Octopus Server (https://octopusdeploy.uservoice.com/forums/170787-general/suggestions/3033637-upgrade-of-octopusserver-through-octopus), I'd suggest that you add a "Download latest version"-button in the server GUI. This would make the upgrade a lot faster, instead of having to navigate to the Octopus web site and find the latest version manually.