I'm interested in stories that span for several years, because if someone installs and maintains something for 1-2 months, then this is not really an indicator of anything. Part of the difficulty comes with system updates, application updates, migration of configuration files, hostile environment like DDoSes of angry people, hacking attempts, deprecated docker containers, incompatible library versions, changed policy of python scripts on some Linux distro, than span over multiple year periods. I would be interested in hearing what people have to say, but including the later subjects as well.
Yeah my self hosting story started in 2003 and involves moving all of those things to many different servers, etc. I had problems with hacking when I used WordPress, the server has been taken over 2 times. Once I stopped that those problems stopped too. And because I have only 1 person instances I don't get much attention of angry people.
The depricated PHP version is my biggest problem until now, I used a lib written in PHP 4 which are now incompatible with PHP 8 and I can't easily rewrite it to make it compatible. So this one is still running on PHP 7, but I will need to do something about it in the future. The best would be to export everything into static HTML but that's also not quite straight forward.
I like your music by the way (Hoggatah)!