I recognize this will vary depending on how much you self-host, so I’m curious about the range of experiences from the few self-hosted things to the many self-hosted things.
Also how might you compare it to other maintenance of your other online systems (e.g. personal computer/phone/etc.)?
If you set it up really well, you’ll probably only need to invest maybe an hour or so every week or two. But it also depends on what kind of maintenance you mean. I spend a lot of time downloading things and putting them in the right place so that my TV is properly entertaining. Is that maintenance? As for updating things, I’ve set up most of that to be automatic. The stuff that’s not automatic, like pulling new docker images, I do every couple weeks. Sometimes that involves running update scripts or changing configs. Usually it’s just a couple commands.