Every time I go the self hosting route, everything goes smoothly for awhile, and then decides to break 6 months down the line, and I have to waste a Saturday figuring it all out and upgrading things. Not what I want to do with my weekend, when I'm already doing software dev and maintenance for work. This happens even for super dependable, well written self hosted software.

On the other hand, maybe AI can help remove some of that pain for me now. Just have Claude figure out what's wrong. (Until it decides to hallucinate something, and makes things worse)