I recommend, reading the release changelogs actively. For most services you can just put the github release page in an RSS reader to get a notification when a new release hits, so you can quickly look for any breaking changes, also this will give you info about new features.
I have been using watchtower for a few years. No problems with auto updates so far, but keep your backup handy.
To not have to deploy software on the server. You can connect to any Linux Server you want and get that information.