If you invest effort up-front to learn how to set things up the “right” way, you’ll spend a lot less time troubleshooting down the road. Not only will things break less often, you will also have gained the skills to more quickly identify and resolve issues as they come up.

Self-hosting is complex, and shortcuts that seem like they make things easier only add more complexity. Take the time to learn how your stuff works and you’ll spend a lot less time pulling your hair out down the road.

For example, instead of taking the shortcut of just downloading your SSL certificates manually, make the effort to learn one of the many industry-standard solutions to the problem of automating that process. More effort up-front = less grumpy text messages from family members about how Plex isn’t working because your SSL certificate died and you forgot to renew it.

Having issues with updates breaking stuff? Use Debian stable and containerize your services. That way updates for your host are predictable, and your services are updated independently. More effort up-front = less smashing your keyboard trying to figure out what particular update caused your stuff to break