Seems people are already making great recommentations.
Personally I also use docker-compose, a WireGuard VPN and an Nginx-Server to proxy/ssl-terminate all my services to my VPN or the Internet.
Just host whatever you like/need. Something like Nextcloud is probably a solid start.
Btw, I have not seen it mentioned here, but awesome-Lists are a thing on github where people collect various gems for certain categories. Here is the one for self-hosting which I have used extensively and really like: https://github.com/awesome-selfhosted/awesome-selfhosted
Also, when you start hosting more than 2-3 services, keeping them up-to-date might become a hassle which you can forget. For docker-based hosting I’d recommend you setup watchtower, which can keep your servives up-to-date for you.
Probably depends. There are some services which I know are rock solid and have never failed me when auto-updating in 2+ years now.
However you are right that it can cause issues. I forgot to mention monitoring totally. My bad. A service like uptime kuma is really worth having for that reason. For a few services that really saved me a few times tbh. I set it up to broadcast status changes to a telegram channel and a special mail inbox. But it can seemingly use any and all services under the sun.
If you only have a handful of services, manual updating is good for learning and can prevent problems by seeing them immediately. However once you have so many services that you can’t possibly update them all or have the motivation to, it’s better to let them auto-update and have a service like uptime kuma notifiy you if something goes wrong imo.
As with all things in the world, it’s matter of striking the right balance of tradeoffs.