I’m an infrastructure guy, I manage a few datacenters that host some backends for ~100,000 IoT devices and some web apps that serve a few million requests a day each. It sounds like a lot, but the only real difference between my work and yours is that at the scale I’m working with, things have to be built in a way that they run uninterrupted with as little interaction from me as possible. You see fewer GUIs, and things stop being super quick and easy to initially get up and running, but the extra effort spent architecting things right rewards you with a much lighter troubleshooting and firefighting workload.

You sorta stop being a mechanic that maintenances and fixes problem cars, and start being an engineer that builds cars to have as few problems as possible. You lose the luxury of being able to fumble around under a car and visually find an oil filter to change, and start having to make decisions on where to put the oil filter from scratch, but to me it is far more rewarding and satisfying. And ultimately the way that self hosting works these days, it has embraced the latter over the former. It’s just a different mindset from the legacy click-ops sysadmin days of IT.

What this looks like to me in your example is, when I have users of my selfhosted stuff complain about something not working, I’m not envisioning yet another car rolling into the shop for me to fix. I envision a puzzle that must be solved. Something that needs optimization or rearchitecting that will make the problem that user had go away, or at the very least fix itself, or alert me so I can fix it before the user complains.

This paradigm I work under is more work, but the work is rewarding and it’s “fun” when I identify a problem that needs solving and solve it. If that isn’t “fun” to you, then all you’re left is the bunch more work part.

So ultimately what you need to figure out is what your goal is. If you’re not interested in this new paradigm and you just want turnkey solutions there are ways of self hosted that are more suited to that mindset. You get less flexibility, but there’s less work involved. And to be clear there’s absolutely nothing wrong with that. At the end of the day you have to do what works for you.

My recommendations to you assuming you just want to self hosted with as little work and maintenance as possible:

• Stick with projects that are simple to set up and are low maintenance. If a project seems like a ton of work get going, just don’t use it. Take the time to shop around for something simpler. Even I do this a lot.
• Try some more turn key self hosting solutions. Anything with an App Store for applications. UnRAID, CasaOS, things of that nature that either have one click deploy apps, or at least have pre-filled templates where all you need to do is provide a couple variable values. You won’t learn as much career wise this way, but it’ll take a huge mental load off.
• When it comes to tools your family is likely to depend on and thus complain about, instead of selfhosting those things perhaps look for a non-big tech alternative. For example, self hosting email can be a lot of work. But you don’t have to use Gmail either. Move your family to ProtonMail or Tutanota, or other similar privacy friendly alternatives. Leave your self hosting for less critical apps that nobody will really care if it goes down and you can fix at your leisure.